| Date | Opponent | Result | Score | Comments |
| 2023-03-29 | Sharon High School | Win | 4 - 0 | |
| 2023-03-29 | Monomoy Regional High School | Win | 3 - 0 | |
| 2023-03-30 | Sandwich High School | Win | 4 - 0 | |
| 2023-04-05 | At Hingham High School | Win | 3 - 0 | |
| 2023-04-05 | Boston College High School | Win | 5 - 0 | |
| 2023-04-08 | Belmont Hill School | Win | 3 - 0 | |
| 2023-04-08 | St John's Prep | Win | 2 - 0 | |
| 2023-04-08 | Barnstable HS | Win | 2 - 0 | |
| 2023-04-12 | St George's School | Loss | 1 - 4 | |
| 2023-04-14 | At Moses Brown School | Win | 4 - 0 | |
| 2023-04-15 | Cape Cod Academy | Win | 2 - 0 | |
| 2023-04-15 | At Portland High School | Win | 2 - 0 | |
| 2023-04-15 | Lincoln Academy | Win | 2 - 0 | |
| 2023-04-15 | Boothbay Regional High School | Win | 2 - 0 | |
| 2023-04-21 | At Portsmouth Abbey School | Win | 3 - 2 | |
| 2023-04-22 | Barrington High School | Win | 4 - 1 | |
| 2023-04-22 | Milton Academy | Win | 4 - 1 | |
| 2023-04-22 | Marthas Vineyard RHS | Win | 3 - 0 | |
| 2023-04-26 | At St George's School | Loss | 1 - 4 | |
| 2023-04-29 | At Salisbury School | Win | 3 - 0 | |
| 2023-04-29 | At Portland High School | Win | 5 - 0 | |
| 2023-04-29 | St. John Paul II High School (MA) | Win | 1 - 0 | Forfeit. Not enough sailors to finish the meet |
| 2023-04-29 | At Hotchkiss School | Win | 3 - 2 |