May 21, 2023 @ 12:53:56 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| 2023 Illinois State Championships | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | State Championship | 2 Divisions | Official | 5/8 | |
| May Madness Regatta | Pewaukee Lake Sailing School | Promotional | 2 Divisions | Official | 7/17 | |
| 2023 May 6 Regatta @ Sheridan Shore | Sheridan Shore | In-District | 1 Division | Official | 4,9/16 | |
| Saturday 22 @ CYC Regatta | Chicago Yacht Club - Belmont | In-League | 1 Division | Official | 21/21 | |
| MISSA Central Baker Qualifier | Lake Forest Sailing | District Champ Qualifier | Team | Official | 10/10 | |
| Central Mallory Qualifier | Lincoln Park | League Championship | 2 Divisions | Official | 12/16 | |
| CYC 2023 MISSA Icebreaker | New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-League | 2 Divisions | Official | 15/15 |