May 2, 2023 @ 12:47:29 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| 45th Massachusetts State High School Championship | Milton Academy | Promotional | 2 Divisions | Official | 2/13 | |
| NESSA Team Racing Tournament (Terk Trophy) | Unregistered-NESSA | District Tournament | Team | Official | 3/8 | |
| Freshman/Sophomore Regatta | Sharon | In-League | 2 Divisions | Official | 15/17 | |
| NESSA Fleet Racing Championship (O'Day Trophy) | Tabor Academy | District Championship | 2 Divisions | Official | 6/17 | |
| O'day Qualifier - SailMaine | Greely - Maine | District Champ Qualifier | 2 Divisions | Official | 4/17 | |
| Clipper Challenge | SailMaine | In-League | Team | Pending | 1/9 |