| Event | Dates | Location |
|---|
|
| Severn Sailing Association Spring Tune-Up | April 28, 29 | Annapolis |
|
| Fleet Setup Day | May 12 | CPYC |
| Fleet Eliminations (2) | May 19 | CPYC |
| 4rd Annual Skippers Choice | May 20 | CPYC |
| Captain Morgan | May 20 | Northport Bay |
| Fleet Eliminations (2) | May 26 | CPYC |
|
| Fleet Eliminations (2) BLOWN OUT | June 2 | CPYC |
| JFK Regatta | June 2, 3 | CPYC |
| Wednesday Night Racing | June 6 | CPYC |
| Fleet Eliminations (2) | June 9 | CPYC |
| Wednesday Night Racing | June 13 | CPYC |
| Arms White | June 16, 17 | Milford |
| Wednesday Night Racing | June 20 | CPYC |
| Districts | June 22, 23, 24 | CPYC |
| Wednesday Night Racing | June 27 | CPYC |
| Fleet Eliminations (2) | June 30 | CPYC |
|
| Summer Series | July 7 | CPYC |
| Mars Venus | July 7, 8 | Greenwood Lake |
| Wednesday Night Racing | July 11 | CPYC |
| Summer Series | July 14 | CPYC |
| Wednesday Night Racing | July 18 | CPYC |
| Ned Hay (Beanpot I) | July 21, 22 | Rockport |
| Wednesday Night Racing | July 25 | CPYC |
| Atlantic Coast Masters | July 28, 29 | Westport, CT |
|
| Wednesday Night Racing | Aug 1 | CPYC |
| Sunapee Open | Aug 4, 5 | Lake Sunapee |
| Wednesday Night Racing | Aug 8 | CPYC |
| Make-a-Wish/Secy's Cup (Beanpot II) | Aug 11, 12 | CPYC |
| Picken Memorial | Aug 11, 12 | Great South Bay |
| Wednesday Night Racing | Aug 15 | CPYC |
| Bill Gray | Aug 18 | Hingham Yacht Club |
| Wednesday Night Racing | Aug 22 | CPYC |
| Star North Americans | Aug 23-Sep 1 | Milford, CT |
|
| Pine Trophy | Sep 8, 9 | CPYC |
| Bedford Pitcher | Sep 15, 16 | Westport, CT |
| Nutmegs | Sep 22, 23 | Milford, CT |
|
| Octoberfest Wind-up | Oct 6, 7 | CPYC |
|