May 16, 2026 @ 19:59:50 EDT
| Name | Host | Type | Scoring | Last race | Place(s) |
|---|---|---|---|---|---|
| National Invitational Tournament (Founders Trophy) | Milton Academy | National Invitational | Team | 65 | 4/12 |
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| 2026 NESSA Fleet Racing Championship(O'Day Trophy) | Hyannis YC | District Championship | 2 Divisions | Official | 11/18 | |
| 2026 NESSA Team Racing Champs (Presidents Trophy) | St. George's | District Championship | Team | Official | 8/8 | |
| 2026 NESSA O'Day Qualifier - Hyannis, MA | Hyannis YC | District Champ Qualifier | 2 Divisions | Official | 2/14 | |
| Broken Tiller Independent School Invitational | Milton Academy | Promotional | 1 Division | Pending | 3,7,8/12 | |
| Dorchester Bay Super Saturday | Milton Academy | In-District | Team | Pending | 1/9 | |
| Clipper Challenge 2026 | SailMaine | In-District | Team | Official | 1/7 |