| Date | Opponent | Result | Score | Comments |
| 2023-04-04 | At Old Rochester Regional High School | Win | 5 - 0 | |
| 2023-04-05 | At Moses Brown School | Win | 3 - 2 | |
| 2023-04-06 | Nauset Regional High School | Win | 4 - 1 | |
| 2023-04-11 | At Bishop Stang High School | Win | 3 - 0 | |
| 2023-04-12 | Wellesley High School | Loss | 2 - 3 | |
| 2023-04-15 | At Moses Brown School | Win | 3 - 0 | |
| 2023-04-15 | Marthas Vineyard RHS | Loss | 1 - 3 | |
| 2023-04-15 | Portsmouth Abbey School | Loss | 0 - 3 | |
| 2023-04-15 | Hotchkiss School | Loss | 0 - 3 | |
| 2023-04-25 | At Barnstable HS | Win | 2 - 0 | |
| 2023-04-25 | Boston College High School | Win | 2 - 0 | |
| 2023-04-25 | At St. John Paul II High School (MA) | Win | 2 - 0 | |
| 2023-04-27 | Falmouth High School | Win | 3 - 1 | |
| 2023-04-28 | At St George's School | Loss | 0 - 3 | |
| 2023-04-28 | North Kingstown High School | Win | 3 - 0 | |
| 2023-04-29 | At Sharon High School | Loss | 0 - 3 | |
| 2023-04-29 | Marthas Vineyard RHS | Loss | 2 - 3 | |
| 2023-04-29 | Barrington High School | Loss | 0 - 3 | |
| 2023-05-04 | Sturgis Charter School | Loss | 0 - 3 | |
| 2023-05-09 | Cape Cod Academy | Win | 6 - 0 | yes, we sailed 6 races. |
| 2023-05-17 | At Nantucket High School | Loss | 1 - 3 |