| Date | Opponent | Result | Score | Comments |
| 2023-04-05 | At Barnstable HS | Loss | 0 - 3 | |
| 2023-04-05 | Milton Academy | Loss | 0 - 2 | |
| 2023-04-05 | At St. John Paul II High School (MA) | Loss | 0 - 3 | |
| 2023-04-06 | Old Rochester Regional High School | Win | 3 - 1 | |
| 2023-04-11 | At Nauset Regional High School | Loss | 2 - 3 | |
| 2023-04-13 | Bishop Stang High School | Win | 3 - 2 | |
| 2023-04-15 | Boothbay Regional High School | Win | 2 - 0 | |
| 2023-04-15 | At Portland High School | Loss | 0 - 2 | |
| 2023-04-15 | Tabor Academy | Loss | 0 - 2 | |
| 2023-04-15 | Lincoln Academy | Loss | 0 - 2 | |
| 2023-04-19 | Boston College High School | Loss | 1 - 4 | |
| 2023-04-25 | At Monomoy Regional High School | Win | 4 - 0 | |
| 2023-04-27 | Barnstable HS | Loss | 1 - 4 | |
| 2023-04-29 | Concord Academy | Win | 5 - 0 | |
| 2023-04-29 | Moses Brown School | Loss | 0 - 3 | |
| 2023-05-02 | At Falmouth High School | Loss | 1 - 4 | |
| 2023-05-04 | Dennis-Yarmouth HS | Win | 3 - 0 | |
| 2023-05-09 | At Dartmouth High School | Loss | 0 - 6 | yes, we sailed 6 races. |
| 2023-05-11 | Sturgis Charter School | Win | 4 - 0 | |
| 2023-05-18 | At Marthas Vineyard RHS | Loss | 1 - 3 | |
| 2023-05-22 | Sandwich High School | Win | 4 - 1 | |
| 2023-05-23 | Nantucket High School | Loss | 2 - 3 |