May 2, 2023 @ 12:47:34 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| 45th Massachusetts State High School Championship | Milton Academy | Promotional | 2 Divisions | Official | 7/13 | |
| NESSA Team Racing Tournament (Terk Trophy) | Unregistered-NESSA | District Tournament | Team | Official | 4/8 | |
| NESSA Girls Championship (Herreshoff Trophy) | Moses Brown | District Championship | 2 Divisions | Official | 11/14 | |
| Donald Greene Regatta | Wellesley | District Tournament | 2 Divisions | Official | 2,6/24 | |
| Freshman/Sophomore Regatta | Sharon | In-League | 2 Divisions | Official | 2,10,11/17 | |
| Herreshoff Qualifier - Marion | Tabor Academy | District Champ Qualifier | 2 Divisions | Official | 4/11 | |
| O'day Qualifier - SailMaine | Greely - Maine | District Champ Qualifier | 2 Divisions | Official | 7/17 | |
| Sharon Invitational | 1 Beach St., Sharon, MA | In-District | 2 Divisions | Official | 4,12/20 | |
| Ridge White Classic | Tabor Academy | In-District | Team | Official | 2/5 | |
| Keelboat Kickoff | Courageous Sailing | Promotional | 2 Divisions | Official | 3,5/17 |