Jun 1, 2023 @ 15:43:20 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | District Championship | 2 Divisions | Official | 11/13 | |
| MISSA Great Lakes Championship | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Championship | 2 Divisions | Official | 12/20 | |
| Halloween Spectacular | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 2/20 | |
| Boats n' Bingo Regatta | Columbia Sailing School | In-District | 2 Divisions | Official | 7/8 | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Champ Qualifier | 2 Divisions | Official | 6/16 | |
| MISSA Keelboat Qualifier | Chicago Yacht Club | District Championship | 1 Division | Official | 11/13 | |
| MISSA Great Oaks Qualifier | New Albany/Olentangy/Olentangy Liberty/Olentangy Orange/Thomas Worthington/Westerville Central/Westerville North/Westerville South | In-District | 1 Division | Official | 17/25 | |
| Banks Blackwell Invitational Regatta | Culver Academies | In-District | 2 Divisions | Official | 3,16/17 | |
| MISSA Cressy Radial Qualifier | Macatawa Bay Junior Association | District Championship | Singlehanded | Official | 24/46 | |
| MISSA Cressy Full Qualifier | Macatawa Bay Junior Association | District Championship | Singlehanded | Official | 10/17 | |
| Fall Scramble | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 6,18/28 |