Jun 1, 2023 @ 15:43:24 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Halloween Spectacular | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 17/20 | |
| Boats n' Bingo Regatta | Columbia Sailing School | In-District | 2 Divisions | Official | 3/8 | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Champ Qualifier | 2 Divisions | Official | 12/16 | |
| ZZ Trophy Regatta | Sheridan Shore Sailing School | In-District | 1 Division | Official | 4,7/13 | |
| MISSA Great Oaks Qualifier | New Albany/Olentangy/Olentangy Liberty/Olentangy Orange/Thomas Worthington/Westerville Central/Westerville North/Westerville South | In-District | 1 Division | Official | 21/25 | |
| Banks Blackwell Invitational Regatta | Culver Academies | In-District | 2 Divisions | Official | 5/17 | |
| Fall Scramble | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 1/28 |