| Date | Opponent | Result | Score | Comments |
| 2023-04-05 | Milton Academy | Loss | 0 - 3 | |
| 2023-04-05 | Cape Cod Academy | Win | 3 - 0 | |
| 2023-04-13 | At Sandwich High School | Win | 3 - 0 | |
| 2023-04-25 | Dartmouth High School | Loss | 0 - 2 | |
| 2023-04-25 | Sturgis Charter School | Win | 2 - 0 | |
| 2023-04-27 | Old Rochester Regional High School | Loss | 1 - 4 | |
| 2023-04-29 | At Tabor Academy | Loss | 0 - 1 | Forfeit. Not enough sailors to finish the meet |
| 2023-04-29 | Portland High School | Loss | 0 - 1 | Forfeit. Not enough sailors to finish the meet |
| 2023-05-02 | At Nauset Regional High School | Loss | 2 - 3 | |
| 2023-05-04 | Bishop Stang High School | Win | 2 - 0 | |
| 2023-05-09 | At Monomoy Regional High School | Win | 3 - 0 | |
| 2023-05-11 | Barnstable HS | Loss | 1 - 4 | |
| 2023-05-18 | Dennis-Yarmouth HS | Win | 3 - 0 | |
| 2023-05-23 | At Falmouth High School | Win | 3 - 1 |