| 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 | 5 | May 1 | Sat | Day | CBYRA-NOTB | 0.0 | 453 | Magothy River SA | Spring Fling | | Trial | | results | Info | Results |
| May 1,2 | 6 | May 1,2 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Spring One Design Invitational | | OD | | 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 15,16 | 11 | May 15,16 | Sat,Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Mandeville Races | | Trial | | results | Info | Results |
| May 15 | 12 | May 15 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Minot Light Challenge | | 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 | CBYRA | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Pursuit) | | PUR | | results | Info | Results |
| May 16 | 15 | May 16 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 1 | Y | PUR | pc | results | Info | Results |
| May 19... | 16 | 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 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 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #3 | Y | HCP | | past | Info | Reg Closed |
| 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 2,9,16,23,30,Jul 7 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 2 | | HCP | | results | Info | Results |
| Jun 2,... | 26 | 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 5,6 | 27 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | results | Info | Results |
| Jun 5,6 | 28 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week J70 | | OD | | 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 12,13,26,27 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Summer Series | | HCP | Ovr, PB | results | Info | Results |
| Jun 12 | 31 | Jun 12 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | Trial | | results | Info | Results |
| Jun 12 | 32 | Jun 12 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | CBC, Ovr, WE | results | Info | Results |
| Jun 12 | 33 | Jun 12 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | Q | 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 19,20 | 40 | 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 | 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... | 42 | 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 | 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 | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | OVR | results | Info | Results |
| Jun 25 | 47 | Jun 25 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | results | Info | Results |
| Jun 26 | 48 | Jun 26 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Regatta | | PUR | CBC, Ovr, WE | results | Info | Results |
| Jun 26 | 49 | Jun 26 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational - New Pursuit Race Format | | PUR | H | 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 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Cape Ann Challenge | | HCP | | past | Info | Results |
| Jul 3 | 55 | Jul 3 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races | | PUR | | results | Info | Results |
| Jul 3,... | 56 | 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 | 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 | GMORA-W | 5,239.6 | 71 | Portland YC | Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 4 | 59 | Jul 4 | Sun | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 151st Anniversary | | HCP | Q | past | Info | Results |
| Jul 8,9 | 60 | Jul 8,9 | Thu,Fri | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham Bay Junior Regatta | | Jr | | results | Info | Results |
| Jul 8 | 61 | Jul 8 | Thu | Day | GMORA | 5,236.3 | 73 | Harraseeket YC | 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 10,11 | 63 | Jul 10,11 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Interclubs Regatta | | HCP | | past | Cancelled | Reg Closed |
| Jul 10,11 | 64 | Jul 10,11 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | results | Info | Results |
| Jul 10 | 65 | 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 | 66 | Jul 10 | Sat | Day | SCYA | 7,825.4 | 172 | California YC | M242 Summer Regatta | | OD | | results | Info | Results |
| Jul 11 | 67 | Jul 11 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 2 | Y | PUR | pc | results | Info | Results |
| Jul 11 | 68 | Jul 11 | Sun | Day | GMORA | 5,215.4 | 75 | Southport YC | Round Southport Race | | PUR | Ovr, BB | past | Info | Reg Closed |
| 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 14,21,28,Aug 4,11,18 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 3 | | HCP | | results | Info | Results |
| Jul 14 | 71 | Jul 14 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Greater Boston Rumble II | | HCP | | past | Info | Reg Closed |
| 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 | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | Q | results | Info | Results |
| Jul 17 | 76 | Jul 17 | Sat | Day | GMORA-B | 5,215.4 | 75 | Southport YC | Seguin Island Trophy Race | | PUR | Ovr, BB | past | 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 | MBSA | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Pursuit Race | | PUR | P | results | Info | Results |
| Jul 18 | 79 | Jul 18 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Star Spangled Classic | | HCP | | 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 | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights - Hingham Bay - ORRez Distance Race | Y | HCP | Q, H | results | Info | Results |
| Jul 24 | 83 | Jul 24 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Driftwood Cup | | PUR | | past | Info | Reg Closed |
| Jul 24,25 | 84 | 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 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 30,31 | 86 | 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 30 | 87 | Jul 30 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | OVR, Ovr | results | Info | Results |
| Jul 30... | 88 | Jul 30,31,Aug 1 | Fri,... | Day | GYA | 6,164.0 | 534 | Gulfport YC | GYA Offshore Challenge Cup | | HCP | | results | Info | Results |
| Jul 31 | 89 | Jul 31 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | HCP | Q | results | Info | Results |
| Jul 31... | 90 | 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... | 91 | 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 | 92 | 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 |
| 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 | 94 | Aug 3 | Tue | Day | GMORA | 5,239.6 | 71 | Portland YC | Maine State Optimist Championships and PYC 420 Invitational | | Jr | | results | Info | Results |
| Aug 3,4 | 95 | Aug 3,4 | Tue,Wed | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | n-10 Open Championship | | 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 7,8 | 100 | Aug 7,8 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | | past | Info | Results |
| Aug 7 | 101 | Aug 7 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHOD Race Day | | HCP | | results | Info | Results |
| Aug 7 | 102 | 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 | 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 | 104 | 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 | 105 | Aug 14 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races (#2) | | PUR | | results | Info | Results |
| Aug 14,15 | 106 | Aug 14,15 | Sat,Sun | Day | GMORA | 0.0 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | Ovr, WE, BB, PB | 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-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC BHOOD Regatta | | HCP | | past | Info | Reg Closed |
| 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-W | 5,239.7 | 144 | Handy Boat | 49th Annual Handy Boat/Hallett Sails Regatta | | HCP | Ovr, WE | results | Info | Results |
| 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 | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race | | PUR | P | results | Info | Results |
| Sep 11 | 125 | 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 11,12 | 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 | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 3 | Y | PUR | pc | results | Info | Results |
| Sep 12 | 128 | Sep 12 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Sep 12 | 129 | Sep 12 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R. Hodder Ocean Race | | HCP | | past | Info | |
| Sep 14 | 130 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | King of the Hill | | PUR | | results | Info | Results |
| Sep 14 | 131 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | Cruising Championship | | PUR | | results | Info | Results |
| Sep 18 | 132 | 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 | 133 | 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 | 134 | Sep 18 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | Q | results | Info | Results |
| Sep 18 | 135 | Sep 18 | Sat | OvrNt | GMORA | 5,192.9 | 74 | Rockland YC | Maine Rocks-Single and Double Handed | | HCP | Ovr, PB | results | Info | Results |
| Sep 18 | 136 | 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 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 | Day | MBSA | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | P | results | Info | Results |
| Sep 25 | 140 | Sep 25 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti Team Race | | Soc | | past | Info | RSVP Closed |
| 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 | GMORA-W | 5,239.6 | 71 | Portland YC | The Lightship Race - Fall Series Race #3 | Y | HCP | WE | past | Info | Reg Closed |
| Oct 2 | 145 | Oct 2 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Leukemia Cup Regatta | | HCP | | results | Info | Results |
| 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 |