May 2, 2023 @ 12:47:24 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| 45th Massachusetts State High School Championship | Milton Academy | Promotional | 2 Divisions | Official | 11/13 | |
| Donald Greene Regatta | Wellesley | District Tournament | 2 Divisions | Official | 7/24 | |
| O'Day Qualifier - Newport, RI | Ida Lewis YC/ St. George's School | District Champ Qualifier | 2 Divisions | Official | 16/17 | |
| Sharon Invitational | 1 Beach St., Sharon, MA | In-District | 2 Divisions | Official | 13/20 | |
| Keelboat Kickoff | Courageous Sailing | Promotional | 2 Divisions | Official | 7/17 |