  | May 13... | 1 | May 13,20,27,Jun 3,10,17 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC  | Wednesday Evening Spring Series | Y | HCP | | results | Info | Results |
| | May 13... | 2 | May 13,20,27,Jun 3,17 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing  | Hingham Bay Spring Series | Y | HCP | B | results | Info | Results |
| | May 20... | 3 | May 20,27,Jun 3,10,17,24 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC  | Spring Evening Series | Y | HCP | | results | Info | Results |
| | May 23 | 4 | May 23 | Sat | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Memorial Day Regatta | Y | HCP | M | results | Info | Results |
| | May 27... | 5 | May 27,Jun 3,10,17,24 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC Boston PHRF Wed Evening Races - Spring Series | Y | HCP | | results | Info | Results |
| | May 27... | 6 | May 27,Jun 3,10,17,24,Jul 1,8,15,22,29,Aug 5,12,19,26 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC  | WEDNESDAY SUMMER SERIES | | HCP | | results | Info | Results |
| | Jun 5 | 7 | Jun 5 | Fri | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Moon Chase | | PUR | P | results | Info | Results |
| | Jun 7 | 8 | Jun 7 | Sun | Day | MBSA-N | 5,250.6 | 7 | Eastern YC  | EYC Lambert Ocean Race | Y | HCP | M | results | Info | Results |
| | Jun 9,... | 9 | Jun 9,16,23,30,Jul 7,14,21,28,Aug 4,11,18,25,Sep 8 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC  | RYC Tuesday Night Series | | HCP | | results | Info | Results |
| | Jun 10 | 10 | Jun 10 | Wed | Eve | MBSA | 5,255.9 | 12 | Boston Harbor Handicap Racing | Rumble I | | HCP | | results | Info | Results |
| | Jun 12... | 11 | Jun 12,13,14 | Fri,... | Day | MBSA-N | 5,248.6 | 29 | Manchester YC  | Rhodes 19 East Coast Championship | | OD | | results | Info | Results |
| | Jun 13 | 12 | Jun 13 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Regatta | | HCP | Ovr, WE | results | Info | Results |
| | Jun 13 | 13 | Jun 13 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | Q | results | Info | Results |
| | Jun 14 | 14 | Jun 14 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead  | Summerset Regatta | Y | HCP | Q, M | results | Info | Results |
| | Jun 20 | 15 | Jun 20 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC  | Pilot Regatta | | HCP | Ovr, WE | results | Info | Results |
| | Jun 20 | 16 | Jun 20 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Solstice Race | | HCP | Ovr, PB | results | Info | Results |
| | Jun 20 | 17 | Jun 20 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | HBPHRF Solstice Regatta | Y | HCP | H, Q | results | Info | Results |
| | Jun 21 | 18 | Jun 21 | Sun | Day | MBSA | 5,250.6 | 7 | Eastern YC | 21st Annual Hospice Regatta | | HCP | Q, M | past | Info | Results |
| | Jun 24... | 19 | Jun 24,Jul 1,15,22,29 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Hingham Bay Summer Series | Y | HCP | B | results | Info | Results |
| | Jun 24... | 20 | Jun 24,Jul 15,22,Aug 5,12,19 | Wed | Eve | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC  | Wednesday Night Series | | HCP | | results | Info | Results |
| | Jun 24... | 21 | Jun 24,Jul 8,15,22,Aug 5 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Summer Series | Y | HCP | | results | Info | Results |
| | Jun 27 | 22 | Jun 27 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC  | Phil Small Regatta | | HCP | M | results | Info | Results |
| | Jun 27... | 23 | Jun 27,Aug 1,22,30 | Sat,Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC  | CYC Summer PHRF Series | | HCP | Ovr, PB | results | Info | Results |
| | Jun 27 | 24 | Jun 27 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC  | HYC Regatta | | PUR | Ovr, WE | results | Info | Results |
| | Jun 28 | 25 | Jun 28 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | Q | past | Info | Results |
| | Jul 1,... | 26 | Jul 1,8,15,22,29,Aug 5 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Summer Evening Series | Y | HCP | | results | Info | Results |
| | Jul 1,... | 27 | Jul 1,8,15,22,29 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC Boston PHRF Wed Races Summer Series | Y | HCP | | results | Info | Results |
| | Jul 4 | 28 | Jul 4 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta | Y | HCP | Q, M | results | Info | Results |
| | Jul 5 | 29 | Jul 5 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Round Southport Race | | PUR | Ovr, BB | results | Info | Results |
| | Jul 8 | 30 | Jul 8 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Rumble II - Hingham Bay | | HCP | | results | Info | Results |
| | Jul 11 | 31 | Jul 11 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | HBPHRF Scorpion Bowl | Y | HCP | H, Q | results | Info | Results |
| | Jul 11 | 32 | Jul 11 | Sat | Day | MBSA-N | 5,248.2 | 68 | Manchester YC - HBC | S.S. Crocker Memorial Race | | PUR | P | results | Info | Results |
| | Jul 12 | 33 | Jul 12 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Ocean Race | Y | HCP | M | results | Info | Results |
| | Jul 12 | 34 | Jul 12 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Jr. Program Foundation Cup Regatta | | HCP | Ovr, BB | results | Info | Results |
| | Jul 17 | 35 | Jul 17 | Fri | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | Q, M | results | Info | Results |
| | Jul 18,19 | 36 | Jul 18,19 | Sat,Sun | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Penobscot Pursuit | | PUR | Ovr, PB | results | Info | Results |
| | Jul 18 | 37 | Jul 18 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC  | Round the Salvages Pursuit Rac | | PUR | | results | Info | Results |
| | Jul 18,19 | 38 | Jul 18,19 | Sat,Sun | Day | GMORA-W | 5,239.7 | 144 | Handy Boat  | PHRF Maine State Championship | | HCP | Ovr, WE | results | Info | Results |
| | Jul 19 | 39 | Jul 19 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC  | Clemson Chase Race | | PUR | P | past | Info | Results |
| | Jul 20... | 40 | Jul 20,21,22 | Mon,... | Day | MBSA-N | 5,250.6 | 81 | Pleon YC  | Marblehead Junior Race Week | | Jr | | results | Info | Results |
| | Jul 24... | 41 | Jul 24,Aug 21 | Fri | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Classic Yacht Race | | PUR | | results | Info | Results |
| | Jul 25,26 | 42 | Jul 25,26 | Sat,Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Invitational Regatta | | HCP | Ovr, PB | results | Info | Results |
| | Jul 25 | 43 | Jul 25 | Sat | Day | GMORA-B | 5,215.4 | 75 | Southport YC | Seguin Island Trophy Race | | HCP | Ovr, BB | results | Info | Results |
| | Jul 25 | 44 | Jul 25 | Sat | Day | MBSA-S | 5,241.4 | 32 | Scituate Sailing | Scituate Invitational- All Invited | | HCP | Q | results | Info | Results |
| | Aug 1 | 45 | Aug 1 | Sat | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC  | CPYC Youth Regatta to Benefit Make A Wish | | Jr | | results | Info | Results |
| | Aug 1,2 | 46 | Aug 1,2 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | 41st Annual BHYC Regatta | | HCP | Ovr, BB | results | Info | Results |
| | Aug 1 | 47 | Aug 1 | Sat | Day | MBSA-N | 5,253.2 | 30 | Palmers Cove YC  | PCYC Bowditch Race | | HCP | Q, M | results | Info | Results |
| | Aug 1 | 48 | Aug 1 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 21st Annual Pursuit Race to Benefit Make-A-Wish | | PUR | P | results | Info | Results |
| | Aug 1 | 49 | Aug 1 | Sat | Day | MBSA-N | 5,255.8 | 11 | Cottage Park YC | CPYC RegattaTo Benefit Make-A-Wish OD | | OD | | past | Info | Results |
| | Aug 5,... | 50 | Aug 5,19,26,Sep 2,9 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Hingham Bay Fall Series | Y | HCP | B | results | Info | Results |
| | Aug 5,... | 51 | Aug 5,12,19,26,Sep 2,9 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC Boston PHRF Wed Night Races Late Summer Series | Y | HCP | | results | Info | Results |
| | Aug 8 | 52 | Aug 8 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Monhegan Island Races | | HCP | Ovr, WE | results | Info | Results |
| | Aug 9,16 | 53 | Aug 9,16 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodores Cup Series | | PUR | Ovr, BB | results | Info | Results |
| | Aug 10... | 54 | Aug 10,11,12 | Mon,... | Eve | MBSA-N | 5,255.8 | 11 | Cottage Park YC | USA Sailing Junior Olympic Festival | | Jr | | results | Info | Results |
| | Aug 11,12 | 55 | Aug 11,12 | Tue,Wed | Day | GMORA | 5,211.2 | 147 | Southport Jr YC Sailing | Maine State Optimist Championships | | Jr | | results | Info | Results |
| | Aug 12 | 56 | Aug 12 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Rumble III | | HCP | | results | Info | Results |
| | Aug 12... | 57 | Aug 12,19,26,Sep 2,9,16 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | HCP | | results | Info | Results |
| | Aug 12... | 58 | Aug 12,19,26,Sep 2,9,16 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Fall Series | Y | HCP | | results | Info | Results |
| | Aug 15 | 59 | Aug 15 | Sat | Day | MBSA | 5,259.0 | 145 | Flip Flop Regatta  | Flip Flop Regatta - Boston Harbor | | PUR | | results | Info | Results |
| | Aug 15 | 60 | Aug 15 | Sat | Day | GMORA-W | 5,239.7 | 77 | Natl. MS Society | MS Harborfest Regatta | | HCP | Ovr, WE | results | Info | Results |
| | Aug 21... | 61 | Aug 21,22,23 | Fri,... | Day | MBSA-N | 5,252.7 | 142 | Rhodes 19 Fleet 5  | Rhodes 19 National Championship | | OD | | results | Info | Results |
| | Aug 22 | 62 | Aug 22 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC  | Hingham YC Hitchcock Trophy | Y | HCP | H, Q | results | Info | Results |
| | Aug 22 | 63 | Aug 22 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | Ovr, WE | results | Info | Results |
| | Aug 22 | 64 | Aug 22 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Gloucester Ocean Pursuit Race | | PUR | P | results | Info | Results |
| | Aug 23 | 65 | Aug 23 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC JFK Regatta | | HCP | Q | results | Info | Results |
| | Aug 28... | 66 | Aug 28,29,30 | Fri,... | Day | MBSA-N | 0.0 | 4 | Mass Bay Sailing  | ONE Championships | | HCP | H, Q, Ovr | results | Info | Results |
| | Sep 2,... | 67 | Sep 2,9,16,23,30 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | Wednesday Fall Series | | HCP | | results | Info | Results |
| | Sep 5 | 68 | Sep 5 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Schooner Festival PHRF Race | | HCP | | results | Info | Results |
| | Sep 7 | 69 | Sep 7 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sailing Heals Pursuit Race | | PUR | P | results | Info | Results |
| | Sep 12 | 70 | Sep 12 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | Q, M | results | Info | Results |
| | Sep 12 | 71 | Sep 12 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club  | AROUND ISLESBORO RACE | | HCP | Ovr, PB | results | Info | Results |
| | Sep 19 | 72 | Sep 19 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC  | HYC Great Chase Race | | PUR | P | results | Info | Results |
| | Sep 19 | 73 | Sep 19 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Race #1 | Y | HCP | Ovr, WE | results | Info | Results |
| | Sep 19 | 74 | Sep 19 | Sat | Day | GMORA | 5,192.9 | 74 | Rockland YC | Maine Rocks Race | | HCP | Ovr, PB | results | Info | Results |
| | Sep 20 | 75 | Sep 20 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R Hodder Regatta | Y | HCP | M | results | Info | Results |
| | Sep 20 | 76 | Sep 20 | Sun | Day | GMORA-W | 5,239.7 | 144 | Handy Boat | 43rd Annual Handy Boat Service/Hallet Sails Regatta | | HCP | | results | Info | Results |
| | Sep 26 | 77 | Sep 26 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Patton Bowl | | HCP | M | results | Info | Results |
| | Sep 26 | 78 | Sep 26 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | HBPHRF Chowder Cup | Y | HCP | H, Q | results | Info | Results |
| | Sep 26,27 | 79 | Sep 26,27 | Sat,Sun | Day | GMORA-W | 5,239.5 | 85 | Etchells Fleet 27 @ Portland YC  | Etchells Lobster Bowl Regatta | | OD | | results | Info | Results |
| | Sep 26 | 80 | Sep 26 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | PYC Lightship Race Sept 26 | Y | HCP | Ovr, WE | results | Info | Results |
| | Sep 26 | 81 | Sep 26 | Sat | Day | PSA | 5,255.9 | 36 | Piscataqua Sailing Association  | Gosport Regatta | | PUR | | results | Info | Results |
| | Sep 27 | 82 | Sep 27 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Fall Series | | HCP | Q, M | results | Info | Results |
| | Oct 3 | 83 | Oct 3 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Race #2 | Y | HCP | Ovr, WE | results | Info | Results |
| | Oct 10 | 84 | Oct 10 | Sat | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Marblehead Chowder Cup | | HCP | Q, M | results | Info | Results |
| | Oct 10 | 85 | Oct 10 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Fall Race #3 | Y | HCP | Ovr, WE | results | Info | Results |
| | Oct 11 | 86 | Oct 11 | Sun | Day | MBSA-S | 5,259.2 | 16 | Boston Harbor Now | Boston Harbor Islands Regatta | | PUR | P | results | Info | Results |
| | Nov 13 | 87 | Nov 13 | Fri | Eve | GMORA | 5,240.0 | 70 | GMORA  | Awards Evening | | Soc | | results | Info | RSVP Closed |
| | Nov 20 | 88 | Nov 20 | Fri | Eve | ALL | 0.0 | 4 | Mass Bay Sailing | MBSA Awards Dinner | | Soc | | results | Info | RSVP Closed |
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