Jun 1, 2023 @ 15:43:26 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | District Championship | 2 Divisions | Official | 6,7,13/13 | |
| Halloween Spectacular | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 13/20 | |
| Art Johnson | Mahtomedi/Mounds Park Academy/Mounds View/White Bear Lake | In-District | 2 Divisions | Official | 15,17/22 | |
| Boats n' Bingo Regatta | Columbia Sailing School | In-District | 2 Divisions | Official | 4/8 | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Champ Qualifier | 2 Divisions | Official | 8/16 | |
| ZZ Trophy Regatta | Sheridan Shore Sailing School | In-District | 1 Division | Official | 6,8,9,10/13 | |
| MISSA Keelboat Qualifier | Chicago Yacht Club | District Championship | 1 Division | Official | 7/13 | |
| MISSA Great Oaks Qualifier | New Albany/Olentangy/Olentangy Liberty/Olentangy Orange/Thomas Worthington/Westerville Central/Westerville North/Westerville South | In-District | 1 Division | Official | 14/25 | |
| Banks Blackwell Invitational Regatta | Culver Academies | In-District | 2 Divisions | Official | 4,14/17 | |
| MISSA Cressy Radial Qualifier | Macatawa Bay Junior Association | District Championship | Singlehanded | Official | 16/46 | |
| Fall Scramble | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 10/28 |