| 2019 Atlantic Coast Championship | TRYC, BBYRA, OCC | National Invitational | 2 Divisions | | Official | 11/20 |
| Catholic Cup | Sail Black Rock | Two-District | 2 Divisions | | Official | 1/10 |
| 2019 NESSA NKBI Qualifier | Cape Elizabeth | District Champ Qualifier | 1 Division | | Official | 3/8 |
| NESSA Fall Funfes (Gleekman Regatta) | Sharon | In-District | 2 Divisions | | Official | 3/16 |
| Arnold Brown Regatta | MVRHS SAIL MV | In-District | 2 Divisions | | Official | 4/12 |
| Casco Bay Fall Open | SailMaine | In-District | 2 Divisions | | Official | 11/16 |
| Polar Bear Open | Bowdoin College Coastal Studies Center | In-District | Combined | | Official | 1/8 |