May 2, 2023 @ 12:45:55 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| SailMaine Cup | Portland | In-District | 2 Divisions | Official | 4,6,14/19 | |
| Falmouth Regatta | Falmouth Maine | In-District | 2 Divisions | Pending | 5,6/12 | |
| NESSA Great Oaks Quals | Sail Black Rock | District Tournament | 1 Division | Official | 5/10 | |
| Sunday Series #5 Yarmouth | Yarmouth | Promotional | 2 Divisions | Official | 6/6 | |
| Clipper Cup | Yarmouth | In-District | 2 Divisions | Official | 3,5/17 | |
| 2021 NESSA Fall Funfest (Gleekman Trophy) | Sharon | In-District | 2 Divisions | Official | 8/13 | |
| NESSA NKBI Qualifier | SailMaine | In-District | 1 Division | Official | 4/6 | |
| SailMaine Sunday Series #3 | Cape Elizabeth | In-District | 2 Divisions | Official | 4,7/13 | |
| Caper Classic | Cape Elizabeth | In-District | 2 Divisions | Official | 1,5/15 | |
| Casco Bay Open | Portland | District Champ Qualifier | 2 Divisions | Official | 4/12 |