| MASSA Qualifier for Keelboat Nationals | Key/St. Marys (MD) | District Championship | 1 Division | | Official | 6/7 |
| Day Light Savings Regatta | Rochester Yacht Club | Promotional | 1 Division | | Official | 1,5/7 |
| NYISA-NW Rochester Wednesday Race Night | McQuaid | In-League | 1 Division | | Official | 7,9,15/16 |
| NYISA-NW Keelboat Qualifier | Rochester Yacht Club | League Championship | 1 Division | | Official | 2/5 |
| MASSA Fall Silver Fleet Championship | Tred Avon Yacht Club | District Championship | 2 Divisions | | Official | 17/17 |
| Rochester Fall 2019 Wednesday Night Fleet Race | Brighton | In-League | 1 Division | | Pending | ,/11 |
| NYISA-NW League Qualifier | Pittsford Sutherland | League Championship | 2 Divisions | | Official | 5,15/15 |
| NYISA-NW Fall One - Design Regatta | McQuaid | In-League | 1 Division | | Official | 18,20/21 |
| Chautauqua Lake Fall Invite | Southwestern Central | In-League | 1 Division | | Official | 9,10/12 |
| MASSA Cressy Qualifier Laser | Shore Acres Yacht Club | District Champ Qualifier | Singlehanded | | Official | 8/9 |