| Date | Opponent | Result | Score | Comments |
| 2023-04-08 | Marthas Vineyard RHS | Loss | 0 - 2 | |
| 2023-04-08 | Milton Academy | Loss | 1 - 2 | |
| 2023-04-08 | Lincoln Academy | Loss | 0 - 2 | |
| 2023-04-08 | Cape Elizabeth HS | Win | 2 - 1 | |
| 2023-04-08 | Falmouth HS (ME) | Loss | 0 - 2 | |
| 2023-04-15 | Boothbay Regional High School | Win | 2 - 0 | |
| 2023-04-15 | Cape Cod Academy | Win | 2 - 0 | |
| 2023-04-15 | Tabor Academy | Loss | 0 - 2 | |
| 2023-04-15 | Lincoln Academy | Loss | 0 - 2 | |
| 2023-04-16 | Hotchkiss School | Loss | 0 - 3 | |
| 2023-04-16 | Barrington High School | Loss | 0 - 5 | |
| 2023-04-16 | At St George's School | Loss | 0 - 3 | |
| 2023-04-22 | At Sharon High School | Loss | 0 - 3 | |
| 2023-04-22 | Rogers High School | Win | 3 - 0 | |
| 2023-04-22 | Hingham High School | Win | 3 - 0 | |
| 2023-04-28 | Cape Elizabeth HS | Win | 2 - 1 | |
| 2023-04-29 | Tabor Academy | Loss | 0 - 5 | |
| 2023-04-29 | St. John Paul II High School (MA) | Win | 1 - 0 | Forfeit. Not enough sailors to finish the meet |