| Jan 1 | 1 | Jan 1 | Fri | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Jack Roberts Memorial NYD Race | | PUR | | past | Info | Reg Closed |
| Mar 27... | 2 | Mar 27,Apr 10,18,May 15,16,22 | Sat,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Spring Race Days | | HCP | | results | Info | Results |
| Apr 06 | 3 | Apr 06 | Tue | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Live Zoom Tour of Community Boat Building | | Soc | | past | Info | RSVP Closed |
| Apr 21... | 4 | Apr 21,28,May 5,12,19,26 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 1 | | HCP | | results | Info | Results |
| May 1,2 | 5 | May 1,2 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Spring One Design Invitational | | OD | | results | Info | Results |
| May 1 | 6 | May 1 | Sat | Day | CBYRA-NOTB | 0.0 | 453 | Magothy River SA | Spring Fling | | Trial | | results | Info | Results |
| May 5 | 7 | May 5 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #1 | Y | HCP | | results | Info | Results |
| May 12 | 8 | May 12 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Constitution YC Skippers Meeting | | Soc | | past | Info | RSVP Closed |
| May 12 | 9 | May 12 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #2 | Y | HCP | | results | Info | Results |
| May 13... | 10 | May 13,20,27,Jun 3,10,17,24,Jul 1,8,15,22,29,Aug 5 | Thu | Day | SCYA | 7,825.4 | 172 | California YC | Starlight | | OD | | results | Info | Results |
| May 15 | 11 | May 15 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Minot Light Challenge | | Trial | | results | Info | Results |
| May 15,16 | 12 | May 15,16 | Sat,Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Mandeville Races | | Trial | | results | Info | Results |
| May 16 | 13 | May 16 | Sun | Day | CBYRA | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Time Trial) | | Trial | | results | Info | Results |
| May 16 | 14 | May 16 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 1 | Y | PUR | pc | results | Info | Results |
| May 16 | 15 | May 16 | Sun | Day | CBYRA | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Pursuit) | | PUR | | results | Info | Results |
| May 19 | 16 | May 19 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #3 | Y | HCP | | past | Info | Reg Closed |
| May 19... | 17 | May 19,26,Jun 2,9,16 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Spring Series | | HCP | | results | Info | Results |
| May 19... | 18 | May 19,26,Jun 2,9,23 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Spring Series | Y | HCP | B | results | Info | Results |
| May 20... | 19 | May 20,27,Jun 3,10,17,24,Jul 8,15,22,29,Aug 5,12,19,26,Sep 2,9,16,23,30 | Thu | Eve | GMORA-W | 5,239.6 | 71 | Portland YC | Thursday Night Races | | HCP | | results | Info | Results |
| May 22,23 | 20 | May 22,23 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | J/70 Spring Regatta | | OD | | results | Info | Results |
| May 26... | 21 | May 26,Jun 2,9,16,23,30,Jul 7,14 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series I | Y | HCP | | results | Info | Results |
| May 26... | 22 | May 26,Jun 2,9,16,23,30,Jul 7,14,21,28,Aug 4,18,25,Sep 1,8 | Wed | Day | SCYA | 7,825.4 | 172 | California YC | Sunset Series | | HCP | | results | Info | Results |
| Jun 1 | 23 | Jun 1 | Tue | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Bakers Light Time Trial | | Trial | | past | Info | Results |
| Jun 2,... | 24 | Jun 2,9,16,23,30,Jul 7 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Spring Evening Series | Y | HCP | WNR | results | Info | Results |
| Jun 2,... | 25 | Jun 2,9,16,23,Jul 8,14,21,28,Aug 4,11,18,25 | Wed,... | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Summer Series | | HCP | | results | Info | Results |
| Jun 2,... | 26 | Jun 2,9,16,23,30,Jul 7 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 2 | | HCP | | results | Info | Results |
| Jun 5,6 | 27 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week J70 | | OD | | results | Info | Results |
| Jun 5,6 | 28 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | results | Info | Results |
| Jun 11 | 29 | Jun 11 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #1 | | PUR | | results | Info | Results |
| Jun 12 | 30 | Jun 12 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | Q | results | Info | Results |
| Jun 12 | 31 | Jun 12 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | CBC, Ovr, WE | results | Info | Results |
| Jun 12... | 32 | Jun 12,13,26,27 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Summer Series | | HCP | Ovr, PB | results | Info | Results |
| Jun 12 | 33 | Jun 12 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | Trial | | results | Info | Results |
| Jun 13 | 34 | Jun 13 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Somerset Regatta | | HCP | Q, SH/ | past | Info | Reg Closed |
| Jun 15... | 35 | Jun 15,29,Jul 6,13,20,27,Aug 3,17,24,31,Sep 7,14 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC | RYC Tuesday Night Series | | HCP | | results | Info | Results |
| Jun 16 | 36 | Jun 16 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Greater Boston Rumble I | | HCP | | results | Info | Results |
| Jun 17... | 37 | Jun 17,24,Jul 1,15,22,29,Aug 5,12,19,26,Sep 2 | Thu | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Twilight Series | | OD | | results | Info | Results |
| Jun 18... | 38 | Jun 18,Jul 16,30,Aug 20,Sep 3 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Division 2 Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 18... | 39 | Jun 18,Jul 16,30,Aug 20,Sep 3 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 19... | 40 | Jun 19,Jul 31 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Commodore's Cup races | | HCP | Ovr, BB | results | Info | Results |
| Jun 19 | 41 | Jun 19 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta - Hingham Bay - ORRez Regatta | Y | HCP | Q, H | results | Info | Results |
| Jun 19,20 | 42 | Jun 19,20 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Pilot Regatta | | HCP | CBC, Ovr, WE | results | Info | Results |
| Jun 19 | 43 | Jun 19 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Solstice Race | | HCP | Ovr, PB | results | Info | Results |
| Jun 20 | 44 | Jun 20 | Sun | Day | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | Ted Osius Memorial Regatta | | HCP | | past | Cancelled | Reg Closed |
| Jun 23... | 45 | Jun 23,30,Jul 7,14,21 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Early Summer Series | | HCP | | results | Info | Results |
| Jun 25 | 46 | Jun 25 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | results | Info | Results |
| Jun 25 | 47 | Jun 25 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | OVR | results | Info | Results |
| Jun 26 | 48 | Jun 26 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational - New Pursuit Race Format | | PUR | H | results | Info | Results |
| Jun 26 | 49 | Jun 26 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Regatta | | PUR | CBC, Ovr, WE | results | Info | Results |
| Jun 27 | 50 | Jun 27 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Patton Bowl | | HCP | | results | Info | Results |
| Jun 30... | 51 | Jun 30,Jul 7,21,28,Aug 11 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Summer Series | Y | HCP | B | results | Info | Results |
| Jul 2 | 52 | Jul 2 | Fri | Day | MBSA | 0.0 | 101 | Manchester SA | Green Fleet Regatta for First Time Racers | | Jr | | past | Cancelled | Reg Closed |
| Jul 2 | 53 | Jul 2 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #2 | | PUR | | past | Info | Results |
| Jul 3,... | 54 | Jul 3,11,24,31,Aug 7,14 | Sat,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE | | HCP | PB | results | Info | Results |
| Jul 3 | 55 | Jul 3 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Cape Ann Challenge | | HCP | | past | Info | Results |
| Jul 3 | 56 | Jul 3 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races | | PUR | | results | Info | Results |
| Jul 3 | 57 | Jul 3 | Sat | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC FIRECRACKER - OCEAN RACE | | HCP | Q, SH/ | past | Info | Results |
| Jul 4 | 58 | Jul 4 | Sun | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 151st Anniversary | | HCP | Q | past | Info | Results |
| Jul 4 | 59 | Jul 4 | Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 8 | 60 | Jul 8 | Thu | Day | GMORA | 5,236.3 | 73 | Harraseeket YC | Junior Regatta | | Jr | | results | Info | Results |
| Jul 8,9 | 61 | Jul 8,9 | Thu,Fri | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham Bay Junior Regatta | | Jr | | results | Info | Results |
| Jul 9,... | 62 | Jul 9,10,11 | Fri,... | Day | MBSA-N | 5,242.0 | 38 | Sandy Bay YC | Star Fleet District 1 Championship | | OD | | past | Info | Results |
| Jul 10 | 63 | Jul 10 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | 54th Annual S.S. Crocker Memorial Race | | PUR | P | results | Info | Results |
| Jul 10,11 | 64 | Jul 10,11 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Interclubs Regatta | | HCP | | past | Cancelled | Reg Closed |
| Jul 10 | 65 | Jul 10 | Sat | Day | SCYA | 7,825.4 | 172 | California YC | M242 Summer Regatta | | OD | | results | Info | Results |
| Jul 10,11 | 66 | Jul 10,11 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | results | Info | Results |
| Jul 11 | 67 | Jul 11 | Sun | Day | GMORA | 5,215.4 | 75 | Southport YC | Round Southport Race | | PUR | Ovr, BB | past | Info | Reg Closed |
| Jul 11 | 68 | Jul 11 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 2 | Y | PUR | pc | results | Info | Results |
| Jul 14... | 69 | Jul 14,21,28,Aug 4,11,18 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Summer Evening Series | Y | HCP | WNR | results | Info | Results |
| Jul 14 | 70 | Jul 14 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Greater Boston Rumble II | | HCP | | past | Info | Reg Closed |
| Jul 14... | 71 | Jul 14,21,28,Aug 4,11,18 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 3 | | HCP | | results | Info | Results |
| Jul 16 | 72 | Jul 16 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | Q, OVR | results | Info | Results |
| Jul 17 | 73 | Jul 17 | Sat | Day | GMORA | 5,172.6 | 100 | Kollegewidgwok YC | True Blue Spencer Evans Laser Regatta | | OD | | past | Info | Reg Closed |
| Jul 17 | 74 | Jul 17 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | Ovr, WE | results | Info | Results |
| Jul 17 | 75 | Jul 17 | Sat | Day | GMORA-B | 5,215.4 | 75 | Southport YC | Seguin Island Trophy Race | | PUR | Ovr, BB | past | Info | Results |
| Jul 17 | 76 | Jul 17 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | Q | results | Info | Results |
| Jul 18 | 77 | Jul 18 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | past | Info | Reg Closed |
| Jul 18 | 78 | Jul 18 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Star Spangled Classic | | HCP | | results | Info | Results |
| Jul 18 | 79 | Jul 18 | Sun | Day | MBSA | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Pursuit Race | | PUR | P | results | Info | Results |
| Jul 21... | 80 | Jul 21,28,Aug 4,11,18,25,Sep 1,8 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series II | Y | HCP | | results | Info | Results |
| Jul 22,23 | 81 | Jul 22,23 | Thu,Fri | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Junior Scorpion Bowl Regatta | | Jr | | results | Info | Results |
| Jul 24 | 82 | Jul 24 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Driftwood Cup | | PUR | | past | Info | Reg Closed |
| Jul 24,25 | 83 | Jul 24,25 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Regatta & Shipyard Cup Classics Challenge | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Jul 24 | 84 | Jul 24 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights - Hingham Bay - ORRez Distance Race | Y | HCP | Q, H | results | Info | Results |
| Jul 28... | 85 | Jul 28,Aug 4,11,18,25 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Late Summer Series | | HCP | | results | Info | Results |
| Jul 30 | 86 | Jul 30 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | OVR, Ovr | results | Info | Results |
| Jul 30... | 87 | Jul 30,31,Aug 1 | Fri,... | Day | GYA | 6,164.0 | 534 | Gulfport YC | GYA Offshore Challenge Cup | | HCP | | results | Info | Results |
| Jul 30,31 | 88 | Jul 30,31 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup | Camden Classics Cup | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Jul 31... | 89 | Jul 31,Aug 1 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC RegattaTo Benefit Make-A-Wish One Design | | OD | | results | Info | Results |
| Jul 31... | 90 | Jul 31,Aug 1 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC Youth Regatta to Benefit Make A Wish | | Jr | | results | Info | Results |
| Jul 31 | 91 | Jul 31 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 26th Annual Pursuit Race to Benefit Make-A-Wish | | PUR | P | results | Info | Results |
| Jul 31 | 92 | Jul 31 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | HCP | Q | results | Info | Results |
| Aug 1 | 93 | Aug 1 | Sun | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Gloucester Ocean Pursuit Race | | PUR | P | results | Info | Results |
| Aug 3,4 | 94 | Aug 3,4 | Tue,Wed | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | n-10 Open Championship | | Jr | | results | Info | Results |
| Aug 3 | 95 | Aug 3 | Tue | Day | GMORA | 5,239.6 | 71 | Portland YC | Maine State Optimist Championships and PYC 420 Invitational | | Jr | | results | Info | Results |
| Aug 4 | 96 | Aug 4 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Greater Boston Rumble III | Y | HCP | | results | Info | Results |
| Aug 6 | 97 | Aug 6 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Feeder Race | | HCP | | results | Info | Results |
| Aug 6 | 98 | Aug 6 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #3 | | PUR | | results | Info | Results |
| Aug 7 | 99 | Aug 7 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC | Flip Flop Regatta | | PUR | P | results | Info | Results |
| Aug 7 | 100 | Aug 7 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHOD Race Day | | HCP | | results | Info | Results |
| Aug 7 | 101 | Aug 7 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Round the Salvages Pursuit Race | | PUR | | results | Info | Results |
| Aug 7,8 | 102 | Aug 7,8 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | | past | Info | Results |
| Aug 7,8 | 103 | Aug 7,8 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Seniors | | OD | | past | Info | Results |
| Aug 14,15 | 104 | Aug 14,15 | Sat,Sun | Day | GMORA | 0.0 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Aug 14 | 105 | Aug 14 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham YC Hitchcock Trophy | Y | HCP | Q, H, SH/ | results | Info | Results |
| Aug 14 | 106 | Aug 14 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races (#2) | | PUR | | results | Info | Results |
| Aug 15 | 107 | Aug 15 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC JFK Regatta | | HCP | Q | results | Info | Results |
| Aug 18... | 108 | Aug 18,19,20 | Wed,... | Day | MBSA | 5,252.7 | 142 | Rhodes 19 Fleet 5 | Rhodes 19 National Championships | | OD | | results | Info | Results |
| Aug 18... | 109 | Aug 18,25,Sep 1,8,15 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Fall Series | Y | HCP | B | results | Info | Results |
| Aug 21 | 110 | Aug 21 | Sat | Day | GMORA-W | 5,239.7 | 144 | Handy Boat | 49th Annual Handy Boat/Hallett Sails Regatta | | HCP | Ovr, WE | results | Info | Results |
| Aug 21,22 | 111 | Aug 21,22 | Sat,Sun | Day | SCYA | 7,825.7 | 253 | Womens Sailing Association (SMB) | WOW/WAH | | HCP | | results | Info | Results |
| Aug 21 | 112 | Aug 21 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC BHOOD Regatta | | HCP | | past | Info | Reg Closed |
| Aug 22 | 113 | Aug 22 | Sun | Day | GMORA-E | 5,240.0 | 84 | NE Habor Fleet | The August Cruise | | PUR | Ovr | past | Info | |
| Aug 25... | 114 | Aug 25,Sep 1,8,15,22,29 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | HCP | WNR | results | Info | Results |
| Aug 28,29 | 115 | Aug 28,29 | Sat,Sun | Day | MBSA | 5,250.2 | 1 | Hull YC | SA/D Regatta | | HCP | | past | Info | Reg Closed |
| Aug 29... | 116 | Aug 29,Sep 5,12,19,26 | Sun | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Fall Series | | HCP | | results | Info | Results |
| Aug 29 | 117 | Aug 29 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | P | results | Info | Results |
| Aug 29 | 118 | Aug 29 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | PUR | | results | Info | Results |
| Sep 1,... | 119 | Sep 1,8,15,22,29,Oct 6 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Fall Series | | HCP | | results | Info | Results |
| Sep 4 | 120 | Sep 4 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Bobby Veltman Memorial Race | | HCP | | results | Info | Results |
| Sep 4 | 121 | Sep 4 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Red and White Race | | HCP | OVR | results | Info | Results |
| Sep 6 | 122 | Sep 6 | Mon | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Degrandpre Doublehanded & Family Race | | HCP | | results | Info | Results |
| Sep 6 | 123 | Sep 6 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sail Salem Pursuit Race | | PUR | P | past | Info | |
| Sep 11 | 124 | Sep 11 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Sep 11 | 125 | Sep 11 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race | | PUR | P | results | Info | Results |
| Sep 11,12 | 126 | Sep 11,12 | Sat,Sun | Day | GMORA | 5,239.5 | 85 | Etchells Fleet 27 @ Portland YC | Lobster Bowl Regatta | | OD | | results | Info | Results |
| Sep 12 | 127 | Sep 12 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R. Hodder Ocean Race | | HCP | | past | Info | |
| Sep 12 | 128 | Sep 12 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 3 | Y | PUR | pc | results | Info | Results |
| Sep 12 | 129 | Sep 12 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Sep 14 | 130 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | Cruising Championship | | PUR | | results | Info | Results |
| Sep 14 | 131 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | King of the Hill | | PUR | | results | Info | Results |
| Sep 18 | 132 | Sep 18 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | Q | results | Info | Results |
| Sep 18 | 133 | Sep 18 | Sat | OvrNt | GMORA-P | 5,192.9 | 74 | Rockland YC | Maine Rocks 2.0-Fully Crewed | | HCP | Ovr, PB | results | Info | Results |
| Sep 18 | 134 | Sep 18 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #1 | Y | HCP | FS, Ovr, WE | results | Info | Results |
| Sep 18 | 135 | Sep 18 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup - Hingham Bay - ORRez Regatta | Y | HCP | Q, H, SH/ | results | Info | Results |
| Sep 18 | 136 | Sep 18 | Sat | OvrNt | GMORA | 5,192.9 | 74 | Rockland YC | Maine Rocks-Single and Double Handed | | HCP | Ovr, PB | results | Info | Results |
| Sep 19 | 137 | Sep 19 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Fall Series | | HCP | Q | results | Info | Results |
| Sep 19... | 138 | Sep 19,Oct 2,10,Nov 14,20 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | | results | Info | Results |
| Sep 25 | 139 | Sep 25 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti Team Race | | Soc | | past | Info | RSVP Closed |
| Sep 25 | 140 | Sep 25 | Sat | Day | MBSA | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | P | results | Info | Results |
| Sep 25 | 141 | Sep 25 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #2 | Y | HCP | FS, Ovr, WE | results | Info | Results |
| Sep 26 | 142 | Sep 26 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Marblehead Chowder Cup | | HCP | Q, SH/ | past | Info | |
| Oct 2 | 143 | Oct 2 | Sat | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | P | results | Info | Results |
| Oct 2 | 144 | Oct 2 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Leukemia Cup Regatta | | HCP | | results | Info | Results |
| Oct 2 | 145 | Oct 2 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Lightship Race - Fall Series Race #3 | Y | HCP | WE | past | Info | Reg Closed |
| Oct 3 | 146 | Oct 3 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Shadden #2 | | Jr | | results | Info | Results |
| Oct 3 | 147 | Oct 3 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Bandit Race - Short Handed | | HCP | SH/ | results | Info | Results |
| Oct 6 | 148 | Oct 6 | Wed | Day | MBSA | 5,259.5 | 9 | Constit. YC | Rogue | | PUR | | past | Info | Reg Closed |
| Oct 9 | 149 | Oct 9 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #4 | Y | HCP | FS, Ovr, WE | results | Info | Results |
| Oct 17 | 150 | Oct 17 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Francis Scott Key Classic | | HCP | | results | Info | Results |
| Nov 14 | 151 | Nov 14 | Sun | Day | GYA | 6,225.2 | 483 | New Orleans YC | Allstate Sugar Bowl Regatta HC | | HCP | | results | Info | Results |
| Nov 19 | 152 | Nov 19 | Fri | Eve | MBSA | 0.0 | 4 | Mass Bay Sailing | MBSA Awards Celebration | | Soc | | results | Info | RSVP Closed |
| Dec 11 | 153 | Dec 11 | Sat | Day | SCYA | 0.0 | 244 | SoCal YRG | MdR Inaugural Regatta / ORA SoCal Championship | | HCP | | results | Info | Results |
| Jan 15,16 | 154 | Jan 15,16 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Winter OD J/70 Regatta | | OD | | results | Info | Results |
| Jan 16 | 155 | Jan 16 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Winter OD M242 | | OD | | results | Info | Results |
| Feb 19,20 | 156 | Feb 19,20 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | SCYA MidWinters | | OD | | past | Info | Reg Closed |
| Feb 23 | 157 | Feb 23 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Stories from Graves Light | | Soc | | past | Info | RSVP Closed |
| Feb 26,27 | 158 | Feb 26,27 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harken #1 Optimist Spring Regatta | | Jr | | past | Info | Reg Closed |
| Mar 19 | 159 | Mar 19 | Sat | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #1 - The Stoney Special* | | HCP | | results | Info | Results |
| Mar 25,26 | 160 | Mar 25,26 | Fri,Sat | Day | SCYA | 7,825.4 | 172 | California YC | ILCA-NA Midwinters West | | OD | | past | Info | Reg Closed |
| Mar 30 | 161 | Mar 30 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Bill & Renée Jacobson present The Saga of Verbena | | Soc | | past | Info | RSVP Closed |
| Apr 2,... | 162 | Apr 2,24,May 14,21,22 | Sat,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Spring Race Days | | HCP | | results | Info | Results |
| Apr 10 | 163 | Apr 10 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harris Spring Regatta | Y | HCP | | results | Info | Results |
| Apr 13... | 164 | Apr 13,20,27,May 4,11,18,25,Jun 1,8,15,22,29,Jul 6,13,20,27,Aug 3,10,17,24,31,Sep 7 | Wed | Day | SCYA | 7,825.4 | 172 | California YC | Sunset Series | | HCP | | results | Info | Results |
| Apr 14... | 165 | Apr 14,21,28,May 5,12,19,26,Jun 2,9,16,23,30 | Thu | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Twilights First Half | | HCP | | past | Info | Reg Closed |
| Apr 22 | 166 | Apr 22 | Fri | OvrNt | ALL | 0.0 | 327 | ORA | Newport to Ensenada International Yacht Race | | HCP | | past | Info | Reg Closed |
| Apr 27... | 167 | Apr 27,May 4,11,18,25 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 1 | | HCP | | results | Info | Results |
| Apr 30 | 168 | Apr 30 | Sat | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #2 - TransHarbor Race* | | HCP | | past | Info | Reg Closed |
| May 4 | 169 | May 4 | Wed | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Regata al Sol ORR-Ez Division | | HCP | | past | Info | Reg Closed |
| May 11 | 170 | May 11 | Wed | Eve | MBSA | 5,251.4 | 2 | Hingham Bay Racing | Hingham Bay Spring Skippers Meeting | | Soc | | past | Info | RSVP Closed |
| May 12... | 171 | May 12,19,26,Jun 2,9,16,23,30,Jul 7,14,21,28,Aug 4 | Thu | Day | SCYA | 7,825.4 | 172 | California YC | Starlight | | OD | | results | Info | Results |
| May 15 | 172 | May 15 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 1 | Y | PUR | pc | results | Info | Results |
| May 18 | 173 | May 18 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Constitution YC Skippers Meeting | | Soc | | past | Info | RSVP Closed |
| May 18... | 174 | May 18,25,Jun 1,15,22 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Spring Series | Y | HCP | B | results | Info | Results |
| May 18... | 175 | May 18,25,Jun 1,8,15 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Spring Series | | HCP | | results | Info | Results |
| May 19 | 176 | May 19 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | May Series Race 1 | | OD | | past | Info | Reg Closed |
| May 19... | 177 | May 19,26,Jun 2,9,16,23,29,Jul 7,14,21,28,Aug 11,18,25,Sep 1,8,15,22,29 | Thu,... | Eve | GMORA-W | 5,239.6 | 71 | Portland YC | Thursday Night Races | | HCP | | results | Info | Results |
| May 21,22 | 178 | May 21,22 | Sat,Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Mandeville Races | | Trial | | results | Info | Results |
| May 21 | 179 | May 21 | Sat | Day | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Pursuit) | | PUR | | results | Info | Results |
| May 21 | 180 | May 21 | Sat | Day | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | SCC EWE Spirit Cup in support of EWE Spirit Foundation (Harbor 20 River) | | OD | | past | Info | Reg Closed |
| May 25... | 181 | May 25,Jun 1,15,22,29,Jul 6,13 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series I | Y | HCP | | results | Info | Results |
| May 25... | 182 | May 25,Jun 1,8,15,22,29,Jul 7,13,20,27,Aug 3,10,17,24,31 | Wed,... | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Summer Series | | HCP | | results | Info | Results |
| May 26 | 183 | May 26 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | May Series Race 2 | | OD | | past | Info | Reg Closed |
| Jun 1,... | 184 | Jun 1,8,15,22,29,Jul 6 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Spring Evening Series | Y | HCP | WNR | results | Info | Results |
| Jun 2 | 185 | Jun 2 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series Club Race 1 | Y | OD | Spr, YCS | results | Info | Results |
| Jun 4,5 | 186 | Jun 4,5 | Sat,Sun | Day | GMORA-W | 0.0 | 737 | NE Sailing Assoc. | U.S. Women’s Match Race Qualifier | | OD | | past | Info | Reg Closed |
| Jun 4 | 187 | Jun 4 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights - 22nm | Y | HCP | Q, H | results | Info | Results |
| Jun 4,5 | 188 | Jun 4,5 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | results | Info | Results |
| Jun 4 | 189 | Jun 4 | Sat | Day | MBSA-N | 5,253.2 | 30 | Palmers Cove YC | Mass Bay Shorthanded Regatta | | HCP | | past | Info | Reg Closed |
| Jun 8 | 190 | Jun 8 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Greater Boston Rumble I | | HCP | | results | Info | Results |
| Jun 9 | 191 | Jun 9 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Combined Race 1 /Spring Series Club Race 2 | Y | OD | Spr, YCS | results | Info | Results |
| Jun 10... | 192 | Jun 10,11,12 | Fri,... | Day | MBSA | 5,248.6 | 29 | Manchester YC | Rhodes 19 East Coast Championship | | OD | | past | Info | Reg Closed |
| Jun 11 | 193 | Jun 11 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | CBC, Ovr, WE | results | Info | Results |
| Jun 11... | 194 | Jun 11,12,25,26 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Summer Series | | HCP | Ovr, PB | results | Info | Results |
| Jun 11 | 195 | Jun 11 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | Trial | | results | Info | Results |
| Jun 11 | 196 | Jun 11 | Sat | Eve | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | Ted Osius Memorial Twilight Regatta | | HCP | | past | Info | Results |
| Jun 11 | 197 | Jun 11 | Sat | Day | GMORA | 5,236.3 | 73 | Harraseeket YC | Harraseeket Laser Clinic | | OD | | past | Info | Reg Closed |
| Jun 11 | 198 | Jun 11 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | Q | results | Info | Results |
| Jun 14... | 199 | Jun 14,28,Jul 5,19,26,Aug 2,9,16,23,30 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC | RYC Tuesday Night Series | | HCP | | results | Info | Results |
| Jun 16... | 200 | Jun 16,23,30,Jul 7,14,21,28,Aug 4,11,18,25,Sep 1 | Thu | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Twilight Series | | OD | | results | Info | Results |
| Jun 17 | 201 | Jun 17 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #1 | | PUR | | results | Info | Results |
| Jun 17 | 202 | Jun 17 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | results | Info | Results |
| Jun 17 | 203 | Jun 17 | Fri | OvrNt | NBYA | 0.0 | 591 | Bermuda Race Organizing Committee | Newport Bermuda Race | | HCP | | past | Info | Reg Closed |
| Jun 18 | 204 | Jun 18 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Pilot Regatta | | HCP | CBC, Ovr, WE | results | Info | Results |
| Jun 18 | 205 | Jun 18 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Solstice Race | | HCP | Ovr, PB | results | Info | Results |
| Jun 18 | 206 | Jun 18 | Sat | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #3 - The Malibu & Return Race* | | HCP | | past | Info | Reg Closed |
| Jun 18 | 207 | Jun 18 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta | Y | HCP | Q, H | results | Info | Results |
| Jun 22... | 208 | Jun 22,29,Jul 6,13,20 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Early Summer Series | | HCP | | past | Info | Reg Closed |
| Jun 24 | 209 | Jun 24 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | OVR | results | Info | Results |
| Jun 24... | 210 | Jun 24,Jul 8,22,Aug 5,19,Sep 2 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 24... | 211 | Jun 24,25,26 | Fri,... | Day | GYA | 0.0 | 742 | GYA Challenge Cup | GYA Offshore Challenge Cup | | HCP | | past | Info | Reg Closed |
| Jun 24... | 212 | Jun 24,Jul 8,22,Aug 5,19,Sep 2 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Division 2 Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 25 | 213 | Jun 25 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Cape Ann Challenge | | HCP | | past | Info | Results |
| Jun 25 | 214 | Jun 25 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Regatta | | PUR | CBC, Ovr, WE | results | Info | Results |
| Jun 25 | 215 | Jun 25 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup #1 | | HCP | Ovr, BB | results | Info | Results |
| Jun 26 | 216 | Jun 26 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Patton Bowl | | HCP | | results | Info | Results |
| Jun 29... | 217 | Jun 29,Jul 6,13,27,Aug 3 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Summer Series | Y | HCP | B | results | Info | Results |
| Jul 2,... | 218 | Jul 2,9,17,24,30,Aug 6 | Sat,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE PHRF | | HCP | PB | results | Info | Results |
| Jul 2 | 219 | Jul 2 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Classic Boat Race #1 | | PUR | | results | Info | Results |
| Jul 2 | 220 | Jul 2 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 4 | 221 | Jul 4 | Mon | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 152nd Anniversary | | HCP | Q | past | Info | Results |
| Jul 7,... | 222 | Jul 7,14,21,Aug 4,11,18,25,Sep 1,8,15,22 | Thu | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Twilights Second Half | | HCP | | past | Info | Reg Closed |
| Jul 8 | 223 | Jul 8 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #2 | | PUR | | past | Info | Results |
| Jul 9 | 224 | Jul 9 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational - Pursuit Race | | PUR | H | results | Info | Results |
| Jul 9,10 | 225 | Jul 9,10 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | results | Info | Results |
| Jul 9 | 226 | Jul 9 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | 55th Annual S.S. Crocker Memorial Race | | PUR | P | results | Info | Results |
| Jul 9 | 227 | Jul 9 | Sat | Day | GMORA | 5,215.4 | 75 | Southport YC | Hendricks Head Open Race | | HCP | | past | Info | Reg Closed |
| Jul 9,10 | 228 | Jul 9,10 | Sat,Sun | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Quahog Quest | | HCP | | past | Info | Reg Closed |
| Jul 10 | 229 | Jul 10 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 2 | | PUR | | past | Info | Reg Closed |
| Jul 10 | 230 | Jul 10 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Round Southport Race | | PUR | | past | Info | Reg Closed |
| Jul 13,14 | 231 | Jul 13,14 | Wed,Thu | Day | GMORA | 5,236.3 | 73 | Harraseeket YC | HYC Junior Regatta | | Jr | | past | Info | Reg Closed |
| Jul 13... | 232 | Jul 13,20,27,Aug 3,10,17 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Summer Evening Series | Y | HCP | WNR | results | Info | Results |
| Jul 14,15 | 233 | Jul 14,15 | Thu,Fri | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham Bay Junior Regatta | | Jr | | results | Info | Results |
| Jul 16 | 234 | Jul 16 | Sat | Day | GMORA-B | 5,215.4 | 75 | Southport YC | Seguin Island Trophy Race | | HCP | Ovr, BB | past | Info | Results |
| Jul 16 | 235 | Jul 16 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Gloucester Ocean Pursuit Race | | PUR | P | results | Info | Results |
| Jul 16 | 236 | Jul 16 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | Q | results | Info | Results |
| Jul 16 | 237 | Jul 16 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Casco Bay Fiasco | | HCP | | past | Info | Reg Closed |
| Jul 16,17 | 238 | Jul 16,17 | Sat,Sun | Day | GMORA | 5,172.6 | 100 | Kollegewidgwok YC | True Blue Spencer Evans Laser Regatta | | OD | | past | Info | Reg Closed |
| Jul 17 | 239 | Jul 17 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Ocean Race | | HCP | | past | Cancelled | Reg Closed |
| Jul 17 | 240 | Jul 17 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | past | Info | Reg Closed |
| Jul 20 | 241 | Jul 20 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Greater Boston Rumble II | | HCP | | past | Info | Reg Closed |
| Jul 22 | 242 | Jul 22 | Fri | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl OCS (Day Time) | | HCP | | past | Info | |
| Jul 22 | 243 | Jul 22 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | Q, OVR | results | Info | |
| Jul 23,24 | 244 | Jul 23,24 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | | past | Info | Results |
| Jul 23,24 | 245 | Jul 23,24 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Seniors | | OD | | past | Info | Results |
| Jul 23 | 246 | Jul 23 | Sat | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #4 - KHYC to CBYC | | HCP | | past | Info | Reg Closed |
| Jul 23,24 | 247 | Jul 23,24 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Regatta & Shipyard Cup Classics Challenge | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Jul 25 | 248 | Jul 25 | Mon | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Junior Scorpion Bowl Regatta | | Jr | | results | Info | Results |
| Jul 27... | 249 | Jul 27,Aug 3,10,17,24 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Late Summer Series | | HCP | | past | Info | Reg Closed |
| Jul 27... | 250 | Jul 27,Aug 3,10,24,31,Sep 7 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series II | Y | HCP | | results | Info | Results |
| Jul 29 | 251 | Jul 29 | Fri | OvrNt | SCYA | 0.0 | 762 | Santa Barbara YC / King Harbor YC | Santa Barbara to King Harbor Race - ORR Shadow | | HCP | | past | Info | Reg Closed |
| Jul 29,30 | 252 | Jul 29,30 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup | Camden Classics Cup | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Jul 29 | 253 | Jul 29 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | OVR, Ovr | results | Info | Results |
| Jul 30 | 254 | Jul 30 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 28th CPYC Pursuit Race to Benefit Make-A-Wish | | PUR | | past | Info | Reg Closed |
| Jul 30 | 255 | Jul 30 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | HCP | Q | results | Info | Results |
| Aug 3,4 | 256 | Aug 3,4 | Wed,Thu | Day | MBSA | 5,255.8 | 11 | Cottage Park YC | N-10 Midgets | | Jr | | past | Info | Reg Closed |
| Aug 5 | 257 | Aug 5 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Feeder Race | | HCP | | results | Info | Results |
| Aug 5 | 258 | Aug 5 | Fri | OvrNt | GMORA-W | 5,239.6 | 71 | Portland YC | Monhegan & Seguin Scoring for GMORA | | HCP | Ovr, WE | results | Info | Results |
| Aug 6,7 | 259 | Aug 6,7 | Sat,Sun | Day | SCYA | 7,825.7 | 253 | Womens Sailing Association (SMB) | WOW/WAH | | HCP | | results | Info | Results |
| Aug 6,7 | 260 | Aug 6,7 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC Youth Regatta to Benefit Make A Wish | | Jr | | results | Info | Results |
| Aug 6 | 261 | Aug 6 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC | Flip Flop Regatta | | PUR | P | results | Info | Results |
| Aug 6 | 262 | Aug 6 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup #2 | | HCP | | past | Info | Reg Closed |
| Aug 6,7 | 263 | Aug 6,7 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC RegattaTo Benefit Make-A-Wish One Design/ Snipe New England's | | OD | | results | Info | Results |
| Aug 7 | 264 | Aug 7 | Sun | Day | GMORA-P | 5,189.5 | 275 | Stockton Harbor SC | Turtlehead Trot | | HCP | PB | past | Info | Reg Closed |
| Aug 9,10 | 265 | Aug 9,10 | Tue,Wed | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Battle of the Bay Junior Regatta | | Jr | | past | Info | Reg Closed |
| Aug 10... | 266 | Aug 10,24,31,Sep 7,14 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Fall Series | Y | HCP | B | results | Info | Results |
| Aug 11 | 267 | Aug 11 | Thu | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | N 10 Juniors | | Jr | | past | Info | Reg Closed |
| Aug 12 | 268 | Aug 12 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #3 | | PUR | | results | Info | Results |
| Aug 13 | 269 | Aug 13 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Round the Salvages Pursuit Race | | PUR | | results | Info | Results |
| Aug 13 | 270 | Aug 13 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Classic Boat Race #2 | | PUR | | past | Info | Reg Closed |
| Aug 13 | 271 | Aug 13 | Sat | Day | GMORA | 5,215.4 | 75 | Southport YC | Mark Island Trophy Race | | HCP | | past | Info | Reg Closed |
| Aug 13 | 272 | Aug 13 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham YC Hitchcock Trophy | Y | HCP | Q, H, SH/ | results | Info | Results |
| Aug 13 | 273 | Aug 13 | Sat | Day | GMORA | 0.0 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Aug 13 | 274 | Aug 13 | Sat | Day | SCYA | 7,825.4 | 172 | California YC | Summer Regatta | | OD | | past | Info | Reg Closed |
| Aug 14 | 275 | Aug 14 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 37th Annual JFK Regatta - A Navigator Race | | HCP | Q | results | Cancelled | Reg Closed |
| Aug 15 | 276 | Aug 15 | Mon | Day | GMORA | 5,211.2 | 147 | Southport Jr YC Sailing | Maine State Optimist Championship | | Jr | | past | Info | Reg Closed |
| Aug 17 | 277 | Aug 17 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Greater Boston Rumble III | Y | HCP | | results | Info | Results |
| Aug 20 | 278 | Aug 20 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | Ovr, WE | results | Info | Results |
| Aug 20 | 279 | Aug 20 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Scholarship Race | | HCP | | past | Info | Reg Closed |
| Aug 24... | 280 | Aug 24,31,Sep 7,14,21,28 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | HCP | WNR | results | Info | Results |
| Aug 24... | 281 | Aug 24,31,Sep 7,14,21,28 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 4 | | HCP | | past | Info | Reg Closed |
| Aug 27,28 | 282 | Aug 27,28 | Sat,Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Aug 27,28 | 283 | Aug 27,28 | Sat,Sun | Day | MBSA-S | 5,250.2 | 1 | Hull YC | SA/D Regatta | | HCP | | past | Info | Reg Closed |
| Aug 27 | 284 | Aug 27 | Sat | Day | GMORA-W | 5,239.7 | 144 | Handy Boat | 50th Annual Handy Boat Regatta | | HCP | Ovr, WE | results | Info | Results |
| Aug 28 | 285 | Aug 28 | Sun | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Bud Gardiner Bowl-Cal 20 | | OD | | past | Info | Reg Closed |
| Aug 28 | 286 | Aug 28 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | P | results | Info | Results |
| Aug 28 | 287 | Aug 28 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | PUR | | results | Info | Results |
| Aug 28... | 288 | Aug 28,Sep 4,11,18,25 | Sun | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Fall Sunday Series | | HCP | | past | Info | Reg Closed |
| Sep 3 | 289 | Sep 3 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Bobby Veltman Memorial Race | | HCP | | results | Info | Results |
| Sep 3 | 290 | Sep 3 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Red and White Race | | HCP | OVR | results | Info | Results |
| Sep 7,... | 291 | Sep 7,14,21,28,Oct 5 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Fall Series | | HCP | | results | Info | Results |
| Sep 10 | 292 | Sep 10 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup | Y | HCP | Q, H, SH/ | results | Info | Results |
| Sep 10 | 293 | Sep 10 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr, WE, BB, PB | results | Info | Results |
| Sep 10 | 294 | Sep 10 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | Q | results | Info | Results |
| Sep 11 | 295 | Sep 11 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 3 | | PUR | | past | Info | Reg Closed |
| Sep 14 | 296 | Sep 14 | Wed | Day | SCYA | 7,825.4 | 172 | California YC | King of the Hill | | PUR | | results | Info | Results |
| Sep 14 | 297 | Sep 14 | Wed | Day | SCYA | 7,825.4 | 172 | California YC | Cruising Championship | | PUR | | results | Info | Results |
| Sep 17 | 298 | Sep 17 | Sat | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #5 - The Matt Walsh Race* | | HCP | | past | Info | Reg Closed |
| Sep 17 | 299 | Sep 17 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Lightship Race - Fall Series Race #1 | Y | HCP | WE | past | Info | Reg Closed |
| Sep 17 | 300 | Sep 17 | Sat | OvrNt | GMORA-P | 5,192.9 | 74 | Rockland YC | Maine Rocks | | HCP | Ovr, PB | results | Info | Results |
| Sep 17 | 301 | Sep 17 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race | | PUR | P | results | Info | Results |
| Sep 17,18 | 302 | Sep 17,18 | Sat,Sun | Day | GMORA | 5,239.5 | 85 | Etchells Fleet 27 @ Portland YC | Lobster Bowl Regatta | | OD | | results | Info | Results |
| Sep 18... | 303 | Sep 18,24,Oct 1,9,16,Nov 13,13 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | | results | Info | Results |
| Sep 18 | 304 | Sep 18 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | Manchester Fall Series | | HCP | Q | results | Info | Results |
| Sep 24... | 305 | Sep 24,Oct 1,8 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #2,3&4 | | HCP | | past | Info | Reg Closed |
| Sep 25 | 306 | Sep 25 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Marblehead Chowder Cup | | HCP | | past | Info | Reg Closed |
| Oct 1 | 307 | Oct 1 | Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | P | results | Info | Results |
| Oct 1 | 308 | Oct 1 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | | results | Info | Results |
| Oct 1 | 309 | Oct 1 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Community Sailing Race Week Handicap Classes | | HCP | | results | Info | Results |
| Oct 2 | 310 | Oct 2 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Bandit Race - Short Handed | | HCP | SH/ | results | Cancelled | Reg Closed |
| Oct 2 | 311 | Oct 2 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Shadden #2 | | Jr | | results | Info | Results |
| Oct 2,... | 312 | Oct 2,16,23 | Sun | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | His N Hers Regatta | | HCP | | past | Info | Reg Closed |
| Oct 16 | 313 | Oct 16 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Francis Scott Key Classic | | HCP | | results | Info | Results |
| Nov 13 | 314 | Nov 13 | Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Allstate Sugar Bowl Regatta HC | | HCP | | results | Info | Results |
| Nov 13 | 315 | Nov 13 | Sun | Eve | MBSA | 5,259.5 | 9 | Constit. YC | CYC Annual Meeting and Brunch | | Soc | | past | Info | RSVP Closed |
| Nov 18 | 316 | Nov 18 | Fri | Eve | MBSA | 0.0 | 4 | Mass Bay Sailing | MBSA Awards Celebration | | Soc | | results | Info | RSVP Closed |
| Dec 3 | 317 | Dec 3 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Christmas Regatta | | HCP | | past | Info | Reg Closed |
| Dec 17 | 318 | Dec 17 | Sat | Day | SCYA | 0.0 | 244 | SoCal YRG | ORR San Diego Race #1 | | HCP | | past | Info | Reg Closed |