May 24, 2023 @ 16:11:55 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Cape & Islands Fleet Championship | Barnstable Hyannis YC | League Championship | 2 Divisions | Official | 3/13 | |
| Herreshoff Qualifier - Barnstable | Barnstable HS | In-District | 2 Divisions | Official | 6/7 | |
| NESSA Team Racing Tournament (Terk Trophy) | Connecticut College | District Tournament | Team | Official | 6/7 | |
| O'Day Qualifier @ Hyannis | Hyannis YC/ Barnstable HS | District Champ Qualifier | 2 Divisions | Official | 6/11 |