| Jan 1 | 1 | Jan 1 | Wed | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Jack Roberts Memorial NYD Race | | PUR | | results | Info | Results |
| Jan 4 | 2 | Jan 4 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | William Berger & William Stein Series | | HCP | | results | Info | Results |
| Jan 11 | 3 | Jan 11 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti Team Race | | Soc | | past | Info | RSVP Closed |
| Jan 18 | 4 | Jan 18 | Sat | Day | SCYA | 7,825.4 | 172 | California YC | J/70 Class West Coast Winter Series - #2 | | OD | j70 | results | Info | Results |
| Jan 19 | 5 | Jan 19 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | J/70 Class West Coast Winter Series - #2 Sunday | | OD | | past | Info | Results |
| Feb 2 | 6 | Feb 2 | Sun | Day | FLWEST | 0.0 | 594 | Rat Island Yacht Club | Winter Series #1 | | HCP | | past | Info | Results |
| Feb 8,9 | 7 | Feb 8,9 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | SCYA MidWinters | | HCP | j70 | results | Info | Results |
| Feb 16 | 8 | Feb 16 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Icicle Regatta | | PUR | | results | Info | Results |
| Feb 19... | 9 | Feb 19,Mar 4 | Wed | Eve | FLEAST | 5,696.7 | 609 | St. Augustine YC | FROSTBITE SERIES | | HCP | | results | Info | Results |
| Feb 22,23 | 10 | Feb 22,23 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harken #1 Optimist Spring Regatta | | Jr | | results | Info | Results |
| Feb 23 | 11 | Feb 23 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Mount Gay 1 | | PUR | | results | Info | Results |
| Feb 29 | 12 | Feb 29 | Sat | Day | FLWEST | 0.0 | 605 | Davis Island YC | HILLSBORO BAY | | HCP | | results | Info | Results |
| Feb 29 | 13 | Feb 29 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Match Racing Clinigatta | | Soc | | past | Info | RSVP Closed |
| Mar 1 | 14 | Mar 1 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Mount Gay 2 | | HCP | | past | Info | |
| Mar 14 | 15 | Mar 14 | Sat | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Mount Gay III | | PUR | | past | Info | Results |
| Apr 4,5 | 16 | Apr 4,5 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | J/70 Spring Regatta | | OD | | past | Info | Results |
| Apr 5 | 17 | Apr 5 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harris Spring Regatta | | HCP | | past | Info | Results |
| Apr 23 | 18 | Apr 23 | Thu | Eve | SCYA | 7,825.4 | 172 | California YC | Match Racing Playoff #1 | | Soc | | past | Info | RSVP Closed |
| May 9 | 19 | May 9 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | AYC Spring Race to Oxford | | HCP | | past | Info | Results |
| May 13 | 20 | May 13 | Wed | Eve | LMSRF | 0.0 | 612 | Chicago Area Sail Racing Association | CHICAGO Wednesday Night Racing | | HCP | | past | Info | Results |
| May 15 | 21 | May 15 | Fri | Day | MBSA | 5,241.4 | 32 | Scituate Sailing | Minot Light Challenge | | Trial | | results | Info | Results |
| May 20... | 22 | May 20,27,Jun 3,10,17 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Spring Series | | HCP | | past | Info | Results |
| May 21 | 23 | May 21 | Thu | Eve | SCYA | 7,825.4 | 172 | California YC | Match Racing Playoff #2 | | Soc | | past | Info | RSVP Closed |
| May 23 | 24 | May 23 | Sat | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Memorial Day Regatta | Y | HCP | | past | Cancelled | Reg Closed |
| Jun 1 | 25 | Jun 1 | Mon | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Bakers Light Time Trial | | Trial | | results | Info | Results |
| Jun 3,... | 26 | Jun 3,10,17,24,Jul 1,8 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Spring Evening Series | | PUR | CNR | past | Info | Results |
| Jun 3,... | 27 | Jun 3,10,17,24,Jul 1,8,15,22,Aug 5,12,19,26,Sep 2,9 | Wed | Day | SCYA | 7,825.4 | 172 | California YC | Sunset Series | | HCP | | past | Info | Results |
| Jun 3,... | 28 | Jun 3,10,17,24 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Spring Series | Y | HCP | | past | Info | Results |
| Jun 4,... | 29 | Jun 4,11,18,25,Jul 2,9,16,Aug 6,13,20,27 | Thu | Day | SCYA | 7,825.4 | 172 | California YC | Starlight | | OD | | past | Info | Results |
| Jun 5,7 | 30 | Jun 5,7 | Fri,Sun | Day | MBSA | 5,248.6 | 29 | Manchester YC | Rhodes 19 East Coast Championship | | OD | | past | Info | Results |
| Jun 6 | 31 | Jun 6 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | | past | Cancelled | Reg Closed |
| Jun 10... | 32 | Jun 10,17,24,Jul 1,8 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 1 | | HCP | | results | Info | Results |
| Jun 10... | 33 | Jun 10,17,24,Jul 1,15,22,29,Aug 5,12,19,26 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | WEDNESDAY SUMMER SERIES | | HCP | | results | Info | Results |
| Jun 13... | 34 | Jun 13,14,27,28 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Summer Series | | HCP | Ovr, PB | results | Info | Results |
| Jun 16... | 35 | Jun 16,23,Jul 7,21,28,Aug 4,11,18,Sep 1,8,15,15 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC | RYC Tuesday Night Series | | HCP | | results | Info | Results |
| Jun 19 | 36 | Jun 19 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #1 | | PUR | | past | Info | |
| Jun 20 | 37 | Jun 20 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Jun 20 | 38 | Jun 20 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Solstice Race | | HCP | Ovr, PB | results | Info | Results |
| Jun 21 | 39 | Jun 21 | Sun | Day | CBYRA-A | 5,495.9 | 452 | Sailing Club Chesapeake | Ted Osius Memorial Regatta | | HCP | | results | Info | Results |
| Jun 24... | 40 | Jun 24,Jul 1,8,15,22 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Early Summer Series | | HCP | | past | Info | Results |
| Jun 24 | 41 | Jun 24 | Wed | Eve | MBSA | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Alternative Format Race | Y | HCP | | past | Info | Results |
| Jun 26 | 42 | Jun 26 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race PHRF Fleet | | HCP | | results | Info | Results |
| Jun 26 | 43 | Jun 26 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | results | Info | Results |
| Jun 26 | 44 | Jun 26 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race Masters Challenge | | HCP | | results | Info | Results |
| Jun 26 | 45 | Jun 26 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | | results | Info | Results |
| Jun 26... | 46 | Jun 26,Jul 10,24,Aug 7,21 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 27 | 47 | Jun 27 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational - New Pursuit Race Format | | PUR | | past | Info | Results |
| Jun 27... | 48 | Jun 27,Jul 11 | Sat | Day | GMORA | 5,214.3 | 78 | Boothbay Harbor YC | BHYC 2020 commodores Cup Series | | HCP | | past | Info | Results |
| Jul 3,4 | 49 | Jul 3,4 | Fri,Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 150th Anniversary | | HCP | | past | Info | Results |
| Jul 4 | 50 | Jul 4 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 5 | 51 | Jul 5 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | | past | Cancelled | Reg Closed |
| Jul 5 | 52 | Jul 5 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Summer II | | PUR | | past | Info | Results |
| Jul 7,... | 53 | Jul 7,8,9,16,23,30,Aug 6,13,20,27,Sep 3 | Tue,... | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Twilight Series | | OD | | results | Info | Results |
| Jul 8 | 54 | Jul 8 | Wed | Day | MBSA | 5,251.4 | 2 | Hingham Bay Racing | Bradford Curry Time Trial | | Trial | | past | Info | Results |
| Jul 11 | 55 | Jul 11 | Sat | Day | CBYRA | 0.0 | 576 | Chesapeake Racer Cruiser Association | BOOMERANG - CRCA BOTY SERIES SCORING | | HCP | CNS | results | Info | Results |
| Jul 11 | 56 | Jul 11 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | EYC BOOMERANG | | HCP | | past | Info | Results |
| Jul 11 | 57 | Jul 11 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | | past | Info | Results |
| Jul 12... | 58 | Jul 12,26,Aug 1 | Sun,Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE | | HCP | Ovr, PB | results | Info | Results |
| Jul 12 | 59 | Jul 12 | Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Pilot Regatta | | HCP | WE, Ovr | results | Info | Results |
| Jul 12 | 60 | Jul 12 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | results | Info | Results |
| Jul 15... | 61 | Jul 15,22,29,Aug 5,12 | Wed | Eve | CBYRA-Annap | 0.0 | 623 | Round Bay Sailing Association | RBSA WEDNESDAY SHADOW | | Trial | | results | Info | Results |
| Jul 15... | 62 | Jul 15,22,29,Aug 5,12 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Summer Series | Y | HCP | | results | Info | Results |
| Jul 15... | 63 | Jul 15,22,29,Aug 5,12,19 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 2 | | HCP | | results | Info | Results |
| Jul 15 | 64 | Jul 15 | Wed | Day | MBSA | 5,251.4 | 2 | Hingham Bay Racing | Bradford Curry Time Trial Week 2 | | Trial | | past | Info | Results |
| Jul 15... | 65 | Jul 15,22,29,Aug 5,12,19 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Summer Evening Series | Y | PUR | CNR | past | Info | Results |
| Jul 17 | 66 | Jul 17 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | | results | Info | Results |
| Jul 18,19 | 67 | Jul 18,19 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | past | Info | Reg Closed |
| Jul 18 | 68 | Jul 18 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | WE, Ovr | results | Info | Results |
| Jul 19 | 69 | Jul 19 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Star Spangled Classic | | HCP | | results | Info | Results |
| Jul 19 | 70 | Jul 19 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Round Southport Race | | PUR | | past | Info | Results |
| Jul 22... | 71 | Jul 22,29,Aug 5,12 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Summer Series - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Jul 22... | 72 | Jul 22,29,Aug 5,12,26,Sep 2,9 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing | | HCP | | results | Info | Results |
| Jul 24,25 | 73 | Jul 24,25 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup | Camden Classics Cup | | HCP | | past | Info | Results |
| Jul 24... | 74 | Jul 24,Aug 22 | Fri,Sat | Day | GMORA | 5,214.3 | 78 | Boothbay Harbor YC | BHYC 2020 Annual Classic Race Series | | PUR | | past | Info | Results |
| Jul 25,26 | 75 | Jul 25,26 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Seniors | | OD | | past | Cancelled | Reg Closed |
| Jul 25 | 76 | Jul 25 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Light Houses (scorpion)- Hingham Bay - ORRez Regatta | Y | HCP | | past | Info | Results |
| Jul 25,26 | 77 | Jul 25,26 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | | past | Cancelled | Reg Closed |
| Jul 25 | 78 | Jul 25 | Sat | Day | MBSA | 5,241.4 | 32 | Scituate Sailing | Kids Drive Pursuit Race | | PUR | | results | Info | Results |
| Jul 29... | 79 | Jul 29,Aug 5,12,19,26 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Late Summer Series | | HCP | | results | Info | Results |
| Jul 31 | 80 | Jul 31 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Regatta | | HCP | | results | Info | Results |
| Aug 1,2 | 81 | Aug 1,2 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | past | Info | Results |
| Aug 1 | 82 | Aug 1 | Sat | Day | GMORA | 5,214.3 | 78 | Boothbay Harbor YC | 46th Annual BHYC Regatta | | HCP | PB, WE, Ovr | results | Info | Results |
| Aug 1 | 83 | Aug 1 | Sat | Day | MBSA | 5,253.2 | 8 | Jubilee YC | Phil Small Race | | HCP | | results | Info | Results |
| Aug 1 | 84 | Aug 1 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 26th Annual Pursuit Race to Benefit Make-A-Wish | | PUR | | past | Cancelled | Reg Closed |
| Aug 2 | 85 | Aug 2 | Sun | Day | GMORA-P | 5,189.5 | 275 | Stockton Harbor SC | Turtlehead Trot | | HCP | Ovr, PB | results | Info | Results |
| Aug 6,... | 86 | Aug 6,13,20,27,Sep 3,17,24,Oct 1,8,15,22 | Thu | Eve | LMSRF | 6,095.5 | 334 | Chicago YC | Thursday Night Skyline Series | | Trial | | results | Info | Results |
| Aug 7,8 | 87 | Aug 7,8 | Fri,Sat | OvrNt | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Monhegan Island Race & Seguin Island Sprint | | HCP | WE, Ovr | results | Info | Results |
| Aug 7 | 88 | Aug 7 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #3 | | PUR | | results | Info | Results |
| Aug 7 | 89 | Aug 7 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | | past | Info | Results |
| Aug 8 | 90 | Aug 8 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC | Flip Flop Regatta | | PUR | | results | Info | Results |
| Aug 8 | 91 | Aug 8 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC 2020 BHOD regatta | | HCP | | past | Info | Results |
| Aug 9 | 92 | Aug 9 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Hospice Regatta -- Care Dimensions | | HCP | | past | Cancelled | Reg Closed |
| Aug 10 | 93 | Aug 10 | Mon | Day | CBYRA | 0.0 | 576 | Chesapeake Racer Cruiser Association | CRAB EZ DUAL SCORE | | Trial | | past | Info | Results |
| Aug 12 | 94 | Aug 12 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Rumble III - Hingham Bay - ORRez Regatta | Y | HCP | | past | Cancelled | Reg Closed |
| Aug 15 | 95 | Aug 15 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC 2020 BHOOD regatta | | HCP | | past | Info | Results |
| Aug 15 | 96 | Aug 15 | Sat | Day | GMORA-W | 5,239.7 | 144 | Handy Boat | 48th Annual Handy Boat/Hallett Sails Regatta | | HCP | | results | Info | Results |
| Aug 15 | 97 | Aug 15 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham YC Hitchcock Trophy | Y | HCP | | past | Info | Results |
| Aug 16 | 98 | Aug 16 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC JFK Regatta | | HCP | | past | Cancelled | Reg Closed |
| Aug 19... | 99 | Aug 19,26,Sep 2,9,16 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Flashlight Series - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Aug 19... | 100 | Aug 19,26,Sep 2,9,16 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Fall Series | Y | HCP | | results | Info | Results |
| Aug 22,23 | 101 | Aug 22,23 | Sat,Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Aug 22 | 102 | Aug 22 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | WE, Ovr | results | Info | Results |
| Aug 26... | 103 | Aug 26,Sep 2,9,16,23,30 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | PUR | CNR | past | Info | Results |
| Aug 26... | 104 | Aug 26,Sep 2,9,16,23,30 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 3 | | HCP | | results | Info | Results |
| Aug 27... | 105 | Aug 27,28,29 | Thu,... | Day | MBSA-N | 5,252.7 | 142 | Rhodes 19 Fleet 5 | Rhodes 19 National Championship | | OD | | past | Cancelled | Reg Closed |
| Aug 28 | 106 | Aug 28 | Fri | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Red and White Race | | HCP | | results | Info | Results |
| Aug 30 | 107 | Aug 30 | Sun | Day | GMORA-E | 5,240.0 | 84 | NE Habor Fleet | Max Warburg Trophy | | HCP | Ovr | past | Info | |
| Aug 30 | 108 | Aug 30 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Veuve Clicquot 1 | | HCP | | results | Info | Results |
| Aug 30... | 109 | Aug 30,Sep 6,13,20,27 | Sun | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Fall Sunday Series | | HCP | | results | Info | Results |
| Aug 30 | 110 | Aug 30 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | PUR | Ovr, PB | results | Info | Results |
| Sep 2,... | 111 | Sep 2,9,16,23,30,Oct 7 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | Wednesday Fall Series | | HCP | | results | Info | Results |
| Sep 7 | 112 | Sep 7 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sail Salem Pursuit Race | | PUR | | results | Info | Results |
| Sep 12 | 113 | Sep 12 | Sat | Day | CBYRA | 0.0 | 576 | Chesapeake Racer Cruiser Association | NASS RACE TO THE LIGHTHOUSES - CRCA BOTY SERIES SCORING | | HCP | CNS | results | Info | Results |
| Sep 12 | 114 | Sep 12 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | NASS Race to the Lighthouses | | HCP | | past | Info | Results |
| Sep 12 | 115 | Sep 12 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr, PB | results | Info | Results |
| Sep 12 | 116 | Sep 12 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Sep 13 | 117 | Sep 13 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | Pompano | | PUR | | past | Info | Results |
| Sep 13 | 118 | Sep 13 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R Hodder Regatta | Y | HCP | | results | Info | Results |
| Sep 19 | 119 | Sep 19 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race (Quarantine Edition) | | Trial | | results | Info | Results |
| Sep 19 | 120 | Sep 19 | Sat | Day | MBSA | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | | results | Info | Results |
| Sep 19,20 | 121 | Sep 19,20 | Sat,Sun | Day | GMORA | 5,239.5 | 85 | Etchells Fleet 27 @ Portland YC | Lobster Bowl Regatta | | OD | | results | Info | Results |
| Sep 19 | 122 | Sep 19 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Lightship Race Fall Series Race #1 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Sep 20... | 123 | Sep 20,Oct 3,3,11,17,Nov 15,21 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | HCF | results | Info | Results |
| Sep 26 | 124 | Sep 26 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | AYC Fall Solomons | | HCP | | past | Info | Results |
| Sep 26 | 125 | Sep 26 | Sat | Day | MBSA | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | | results | Info | Results |
| Sep 26 | 126 | Sep 26 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Fall Series Race #2 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Sep 26 | 127 | Sep 26 | Sat | Day | CBYRA | 0.0 | 576 | Chesapeake Racer Cruiser Association | AYC SOLOMONS - CRCA BOTY SERIES SCORING | | HCP | CNS | results | Info | Results |
| Sep 27 | 128 | Sep 27 | Sun | Day | MBSA | 5,250.6 | 7 | Eastern YC | Marblehead Chowder Cup Challenge | | HCP | | results | Info | Results |
| Oct 3 | 129 | Oct 3 | Sat | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | | results | Info | Results |
| Oct 3 | 130 | Oct 3 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Fall Series Race #3 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Oct 3 | 131 | Oct 3 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Leukemia Cup Regatta | | HCP | HCF | results | Info | Results |
| Oct 3 | 132 | Oct 3 | Sat | Day | CBYRA | 0.0 | 451 | Potapskut Sailing Assoication | WISH WE WERE RACING TO ROCK HALL | | HCP | CNS | results | Info | Results |
| Oct 10,10 | 133 | Oct 10,10 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Fall Series Race #4 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Oct 17 | 134 | Oct 17 | Sat | Day | CBYRA | 0.0 | 576 | Chesapeake Racer Cruiser Association | BALT HARBOR CUP - CRCA BOTY SERIES SCORING | | HCP | | past | Info | Results |
| Oct 17 | 135 | Oct 17 | Sat | Day | ALL | 0.0 | 327 | Offshore RA | Baltimore Harbor Cup | | HCP | CNS | past | Info | Results |
| Oct 18 | 136 | Oct 18 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Francis Scott Key Classic | | HCP | | results | Info | Results |
| Nov 15 | 137 | Nov 15 | Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Allstate Sugar Bowl Regatta HC | | HCP | HCF | results | Info | Results |
| Nov 15 | 138 | Nov 15 | Sun | Day | BSA | 4,759.8 | 598 | Bermuda Offshore Cruising Association | TEST | | PUR | | past | Info | Reg Closed |
| Nov 18 | 139 | Nov 18 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Annual Meeting | | Soc | | past | Info | RSVP Closed |
| Dec 01 | 140 | Dec 01 | Tue | Eve | MBSA | 5,259.5 | 9 | Constit. YC | CYC NYD Celebration | | Soc | | past | Info | RSVP Closed |
| Jan 1 | 141 | Jan 1 | Fri | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Jack Roberts Memorial NYD Race | | PUR | | results | Info | Results |
| Mar 27... | 142 | Mar 27,Apr 10,18,May 15,16,22 | Sat,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Spring Race Days | | HCP | HCF | results | Info | Results |
| Apr 06 | 143 | 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... | 144 | 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 | 145 | May 1,2 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Spring One Design Invitational | | OD | | past | Info | Reg Closed |
| May 1 | 146 | May 1 | Sat | Day | CBYRA-NOTB | 0.0 | 453 | Magothy River SA | Spring Fling | | Trial | | past | Info | Reg Closed |
| May 5 | 147 | May 5 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #1 | | HCP | | past | Info | Results |
| May 12 | 148 | May 12 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #2 | | HCP | | past | Info | Reg Closed |
| May 12 | 149 | May 12 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Constitution YC Skippers Meeting | | Soc | | past | Info | RSVP Closed |
| May 13... | 150 | 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 | | past | Info | Results |
| May 15 | 151 | May 15 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Minot Light Challenge | | Trial | | results | Info | Results |
| May 15,16 | 152 | May 15,16 | Sat,Sun | Day | GYA | 6,224.9 | 484 | Southern YC | Mandeville Races | | Trial | | past | Info | Reg Closed |
| May 16 | 153 | May 16 | Sun | Day | CBYRA | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Pursuit) | | PUR | | past | Info | Results |
| May 16 | 154 | May 16 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 1 | | PUR | | past | Info | Reg Closed |
| May 16 | 155 | May 16 | Sun | Day | CBYRA | 5,495.9 | 452 | Sailing Club Chesapeake | SCC Spring Regatta in support of EWE Spirit Foundation (Time Trial) | | Trial | | past | Info | Reg Closed |
| May 19... | 156 | 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 | | results | Info | Results |
| May 19 | 157 | May 19 | Wed | Eve | SCYA | 7,825.4 | 172 | California YC | Before Sunset #3 | | HCP | | past | Info | Reg Closed |
| May 19... | 158 | May 19,26,Jun 2,9,16 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Spring Series | | HCP | | past | Info | Results |
| May 20... | 159 | 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 | | past | Info | Results |
| May 22,23 | 160 | May 22,23 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | J/70 Spring Regatta | | OD | | past | Info | Reg Closed |
| May 26... | 161 | 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 | | HCP | | results | Info | Results |
| May 26... | 162 | 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 | | past | Info | Results |
| Jun 1 | 163 | Jun 1 | Tue | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Bakers Light Time Trial | | Trial | | results | Info | Results |
| Jun 2,... | 164 | 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,... | 165 | Jun 2,9,16,23,30,Jul 7 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 2 | | HCP | | past | Info | Reg Closed |
| Jun 2,... | 166 | Jun 2,9,16,23,30,Jul 7 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Spring Evening Series | | HCP | CNR | past | Info | Results |
| Jun 5,6 | 167 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week J70 | | OD | | past | Info | Reg Closed |
| Jun 5,6 | 168 | Jun 5,6 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | past | Info | Results |
| Jun 11 | 169 | Jun 11 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #1 | | PUR | | past | Info | Reg Closed |
| Jun 12 | 170 | Jun 12 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | | past | Info | Results |
| Jun 12 | 171 | Jun 12 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | WE, Ovr | results | Info | Results |
| Jun 12 | 172 | Jun 12 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | Trial | | past | Info | Results |
| Jun 12... | 173 | 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 13 | 174 | Jun 13 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Somerset Regatta | | HCP | | past | Info | Results |
| Jun 15... | 175 | 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 | 176 | Jun 16 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Greater Boston Rumble I | | HCP | | past | Info | Reg Closed |
| Jun 17... | 177 | 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... | 178 | 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 | | past | Info | Reg Closed |
| Jun 18... | 179 | 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 | 180 | Jun 19,20 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Pilot Regatta | | HCP | WE, Ovr | results | Info | Results |
| Jun 19 | 181 | Jun 19 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Solstice Race | | HCP | Ovr, PB | results | Info | Results |
| Jun 19 | 182 | Jun 19 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Jun 19... | 183 | Jun 19,Jul 31 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Commodore's Cup races | | HCP | | past | Info | Reg Closed |
| Jun 20 | 184 | Jun 20 | Sun | Day | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | Ted Osius Memorial Regatta | | HCP | | results | Cancelled | Reg Closed |
| Jun 23... | 185 | Jun 23,30,Jul 7,14,21 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Early Summer Series | | HCP | | past | Info | Reg Closed |
| Jun 25 | 186 | Jun 25 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | | results | Info | Results |
| Jun 25 | 187 | Jun 25 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | results | Info | Results |
| Jun 26 | 188 | Jun 26 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Regatta | | PUR | | past | Info | Reg Closed |
| Jun 26 | 189 | Jun 26 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational - New Pursuit Race Format | | PUR | | past | Info | Results |
| Jun 27 | 190 | Jun 27 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Patton Bowl | | HCP | | past | Info | Reg Closed |
| Jun 30... | 191 | Jun 30,Jul 7,21,28,Aug 11 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Summer Series | | HCP | | past | Info | Reg Closed |
| Jul 2 | 192 | Jul 2 | Fri | Day | MBSA | 0.0 | 101 | Manchester SA | Green Fleet Regatta for First Time Racers | | Jr | | past | Cancelled | Reg Closed |
| Jul 2 | 193 | Jul 2 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #2 | | PUR | | past | Info | Reg Closed |
| Jul 3 | 194 | Jul 3 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races | | PUR | | past | Info | Reg Closed |
| Jul 3 | 195 | Jul 3 | Sat | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC FIRECRACKER - OCEAN RACE | | HCP | | results | Info | Results |
| Jul 3 | 196 | Jul 3 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Cape Ann Challenge | | HCP | | past | Info | Reg Closed |
| Jul 3,... | 197 | Jul 3,11,24,31,Aug 7,14 | Sat,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE | | HCP | Ovr, PB | results | Info | Results |
| Jul 4 | 198 | Jul 4 | Sun | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 151st Anniversary | | HCP | | past | Info | Results |
| Jul 4 | 199 | Jul 4 | Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 8 | 200 | Jul 8 | Thu | Day | GMORA | 5,236.3 | 73 | Harraseeket YC | Junior Regatta | | Jr | | past | Info | Reg Closed |
| Jul 8,9 | 201 | Jul 8,9 | Thu,Fri | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham Bay Junior Regatta | | Jr | | past | Info | Reg Closed |
| Jul 9,... | 202 | Jul 9,10,11 | Fri,... | Day | MBSA-N | 5,242.0 | 38 | Sandy Bay YC | Star Fleet District 1 Championship | | OD | | past | Info | Reg Closed |
| Jul 10 | 203 | Jul 10 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | 54th Annual S.S. Crocker Memorial Race | | PUR | | past | Info | Reg Closed |
| Jul 10,11 | 204 | Jul 10,11 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | past | Info | Reg Closed |
| Jul 10,11 | 205 | Jul 10,11 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Interclubs Regatta | | HCP | | past | Cancelled | Reg Closed |
| Jul 10 | 206 | Jul 10 | Sat | Day | SCYA | 7,825.4 | 172 | California YC | M242 Summer Regatta | | OD | | past | Info | Reg Closed |
| Jul 11 | 207 | Jul 11 | Sun | Day | GMORA | 5,215.4 | 75 | Southport YC | Round Southport Race | | PUR | | past | Info | Reg Closed |
| Jul 11 | 208 | Jul 11 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 2 | | PUR | | past | Info | Reg Closed |
| Jul 14... | 209 | Jul 14,21,28,Aug 4,11,18 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Summer Evening Series | Y | HCP | CNR | past | Info | Results |
| Jul 14 | 210 | 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... | 211 | Jul 14,21,28,Aug 4,11,18 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 3 | | HCP | | past | Info | Reg Closed |
| Jul 16 | 212 | Jul 16 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | | results | Info | Results |
| Jul 17 | 213 | Jul 17 | Sat | Day | GMORA-B | 5,215.4 | 75 | Southport YC | Seguin Island Trophy Race | | PUR | | past | Info | Reg Closed |
| Jul 17 | 214 | Jul 17 | Sat | Day | GMORA | 5,172.6 | 100 | Kollegewidgwok YC | True Blue Spencer Evans Laser Regatta | | OD | | past | Info | Reg Closed |
| Jul 17 | 215 | Jul 17 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | WE, Ovr | results | Info | Results |
| Jul 17 | 216 | Jul 17 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | | past | Info | Reg Closed |
| Jul 18 | 217 | Jul 18 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Star Spangled Classic | | HCP | | results | Info | Results |
| Jul 18 | 218 | Jul 18 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | results | Info | Results |
| Jul 18 | 219 | Jul 18 | Sun | Day | MBSA | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Pursuit Race | | PUR | | past | Info | Reg Closed |
| Jul 21... | 220 | 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 | | HCP | | past | Info | Reg Closed |
| Jul 22,23 | 221 | Jul 22,23 | Thu,Fri | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Junior Scorpion Bowl Regatta | | Jr | | past | Info | Reg Closed |
| Jul 24 | 222 | Jul 24 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Driftwood Cup | | PUR | | past | Info | Reg Closed |
| Jul 24,25 | 223 | Jul 24,25 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Regatta & Shipyard Cup Classics Challenge | | HCP | | past | Info | Reg Closed |
| Jul 24 | 224 | Jul 24 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights - Hingham Bay - ORRez Distance Race | Y | HCP | | past | Info | Results |
| Jul 28... | 225 | Jul 28,Aug 4,11,18,25 | Wed | Eve | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Late Summer Series | | HCP | | past | Info | Reg Closed |
| Jul 30... | 226 | Jul 30,31,Aug 1 | Fri,... | Day | GYA | 6,164.0 | 534 | Gulfport YC | GYA Offshore Challenge Cup | | HCP | | past | Info | Results |
| Jul 30 | 227 | Jul 30 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | | past | Info | Results |
| Jul 30,31 | 228 | Jul 30,31 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup | Camden Classics Cup | | HCP | | past | Info | Results |
| Jul 31 | 229 | Jul 31 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 26th Annual Pursuit Race to Benefit Make-A-Wish | | PUR | | past | Info | Results |
| Jul 31... | 230 | 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 | | past | Info | Reg Closed |
| Jul 31 | 231 | Jul 31 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | HCP | | past | Info | Results |
| Jul 31... | 232 | 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 | | past | Info | Reg Closed |
| Aug 1 | 233 | Aug 1 | Sun | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Gloucester Ocean Pursuit Race | | PUR | | past | Info | Reg Closed |
| Aug 3 | 234 | Aug 3 | Tue | Day | GMORA | 5,239.6 | 71 | Portland YC | Maine State Optimist Championships and PYC 420 Invitational | | Jr | | past | Info | Reg Closed |
| Aug 3,4 | 235 | Aug 3,4 | Tue,Wed | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | n-10 Open Championship | | Jr | | past | Info | Reg Closed |
| Aug 4 | 236 | Aug 4 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Greater Boston Rumble III | Y | HCP | | past | Info | Results |
| Aug 6 | 237 | Aug 6 | Fri | Eve | MBSA | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #3 | | PUR | | past | Info | Reg Closed |
| Aug 6 | 238 | Aug 6 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Feeder Race | | HCP | | results | Info | Results |
| Aug 7 | 239 | Aug 7 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Round the Salvages Pursuit Race | | PUR | | past | Info | Reg Closed |
| Aug 7 | 240 | Aug 7 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC | Flip Flop Regatta | | PUR | | results | Info | Results |
| Aug 7,8 | 241 | Aug 7,8 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Seniors | | OD | | past | Info | Results |
| Aug 7,8 | 242 | Aug 7,8 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | | past | Info | Results |
| Aug 7 | 243 | Aug 7 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHOD Race Day | | HCP | | past | Info | Reg Closed |
| Aug 14,15 | 244 | Aug 14,15 | Sat,Sun | Day | GMORA | 0.0 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | | past | Info | Reg Closed |
| Aug 14 | 245 | Aug 14 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham YC Hitchcock Trophy | Y | HCP | | past | Info | Results |
| Aug 14 | 246 | Aug 14 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Classic Boat Races (#2) | | PUR | | past | Info | Reg Closed |
| Aug 15 | 247 | Aug 15 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC JFK Regatta | | HCP | | past | Info | Results |
| Aug 18... | 248 | Aug 18,25,Sep 1,8,15 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Wednesday Night Racing - Fall Series | | HCP | | past | Info | Reg Closed |
| Aug 18... | 249 | Aug 18,19,20 | Wed,... | Day | MBSA | 5,252.7 | 142 | Rhodes 19 Fleet 5 | Rhodes 19 National Championships | | OD | | past | Info | Reg Closed |
| Aug 21 | 250 | Aug 21 | Sat | Day | GMORA-W | 5,239.7 | 144 | Handy Boat | 49th Annual Handy Boat/Hallett Sails Regatta | | HCP | | results | Info | Results |
| Aug 21,22 | 251 | Aug 21,22 | Sat,Sun | Day | SCYA | 7,825.7 | 253 | Womens Sailing Association (SMB) | WOW/WAH | | HCP | | past | Info | Reg Closed |
| Aug 21 | 252 | Aug 21 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC BHOOD Regatta | | HCP | | past | Info | Reg Closed |
| Aug 22 | 253 | Aug 22 | Sun | Day | GMORA-E | 5,240.0 | 84 | NE Habor Fleet | The August Cruise | | PUR | Ovr | past | Info | |
| Aug 25... | 254 | Aug 25,Sep 1,8,15,22,29 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | HCP | CNR | past | Info | Results |
| Aug 28,29 | 255 | Aug 28,29 | Sat,Sun | Day | MBSA | 5,250.2 | 1 | Hull YC | SA/D Regatta | | HCP | | past | Info | Reg Closed |
| Aug 29 | 256 | Aug 29 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | PUR | Ovr, PB | results | Info | Results |
| Aug 29... | 257 | Aug 29,Sep 5,12,19,26 | Sun | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Fall Series | | HCP | | past | Info | Reg Closed |
| Aug 29 | 258 | Aug 29 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | | past | Info | Results |
| Sep 1,... | 259 | 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 | 260 | Sep 4 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Red and White Race | | HCP | | results | Info | Results |
| Sep 4 | 261 | Sep 4 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Bobby Veltman Memorial Race | | HCP | | past | Info | Reg Closed |
| Sep 6 | 262 | Sep 6 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sail Salem Pursuit Race | | PUR | | past | Info | |
| Sep 6 | 263 | Sep 6 | Mon | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Degrandpre Doublehanded & Family Race | | HCP | | past | Info | Reg Closed |
| Sep 11 | 264 | Sep 11 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr, PB | results | Info | Results |
| Sep 11 | 265 | Sep 11 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race | | PUR | | results | Info | Results |
| Sep 11,12 | 266 | 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 | 267 | Sep 12 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Sep 12 | 268 | Sep 12 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 3 | | PUR | | past | Info | Reg Closed |
| Sep 12 | 269 | Sep 12 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R. Hodder Ocean Race | | HCP | | past | Info | |
| Sep 14 | 270 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | King of the Hill | | PUR | | past | Info | Reg Closed |
| Sep 14 | 271 | Sep 14 | Tue | Day | SCYA | 7,825.4 | 172 | California YC | Cruising Championship | | PUR | | past | Info | Reg Closed |
| Sep 18 | 272 | Sep 18 | Sat | OvrNt | GMORA | 5,192.9 | 74 | Rockland YC | Maine Rocks-Single and Double Handed | | HCP | | past | Info | Reg Closed |
| Sep 18 | 273 | Sep 18 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #1 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Sep 18 | 274 | Sep 18 | Sat | OvrNt | GMORA-P | 5,192.9 | 74 | Rockland YC | Maine Rocks 2.0-Fully Crewed | | HCP | | past | Info | Reg Closed |
| Sep 18 | 275 | Sep 18 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup - Hingham Bay - ORRez Regatta | Y | HCP | | results | Info | Results |
| Sep 18 | 276 | Sep 18 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | | results | Info | Results |
| Sep 19... | 277 | Sep 19,Oct 2,10,Nov 14,20 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | | past | Info | Reg Closed |
| Sep 19 | 278 | Sep 19 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Fall Series | | HCP | | past | Info | Reg Closed |
| Sep 25 | 279 | Sep 25 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti Team Race | | Soc | | past | Info | RSVP Closed |
| Sep 25 | 280 | Sep 25 | Sat | Day | MBSA | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | | results | Info | Results |
| Sep 25 | 281 | Sep 25 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #2 | Y | HCP | Ovr, FS, WE | results | Info | Results |
| Sep 26 | 282 | Sep 26 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Marblehead Chowder Cup | | HCP | | past | Info | |
| Oct 2 | 283 | Oct 2 | Sat | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | | past | Info | Reg Closed |
| Oct 2 | 284 | Oct 2 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Leukemia Cup Regatta | | HCP | HCF | results | Info | Results |
| Oct 2 | 285 | Oct 2 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Lightship Race - Fall Series Race #3 | | HCP | | past | Info | Reg Closed |
| Oct 3 | 286 | Oct 3 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Bandit Race - Short Handed | | HCP | | past | Info | Reg Closed |
| Oct 3 | 287 | Oct 3 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Shadden #2 | | Jr | | past | Info | Reg Closed |
| Oct 6 | 288 | Oct 6 | Wed | Day | MBSA | 5,259.5 | 9 | Constit. YC | Rogue | | PUR | | past | Info | Reg Closed |
| Oct 9 | 289 | Oct 9 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Series Race #4 | | HCP | | past | Info | Reg Closed |
| Oct 17 | 290 | Oct 17 | Sun | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | Francis Scott Key Classic | | HCP | | results | Info | Results |
| Nov 14 | 291 | Nov 14 | Sun | Day | GYA | 6,225.2 | 483 | New Orleans YC | Allstate Sugar Bowl Regatta HC | | HCP | HCF | results | Info | Results |
| Nov 19 | 292 | Nov 19 | Fri | Eve | MBSA | 0.0 | 4 | Mass Bay Sailing | MBSA Awards Celebration | | Soc | | results | Info | RSVP Closed |
| Dec 11 | 293 | Dec 11 | Sat | Day | SCYA | 0.0 | 244 | SoCal YRG | MdR Inaugural Regatta / ORA SoCal Championship | | HCP | | past | Info | Reg Closed |