May 21, 2023 @ 12:53:57 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 | 3/8 | |
| May Madness Regatta | Pewaukee Lake Sailing School | Promotional | 2 Divisions | Official | 13/17 | |
| 2023 May 6 Regatta @ Sheridan Shore | Sheridan Shore | In-District | 1 Division | Official | 3,6,10/16 | |
| MISSA Central Baker Qualifier | Lake Forest Sailing | District Champ Qualifier | Team | Official | 8/10 | |
| 2023 Spring April 15 JV Regatta | Sheridan Shore | In-District | 1 Division | Official | 3,11/13 | |
| Central Mallory Qualifier | Lincoln Park | League Championship | 2 Divisions | Official | 9/16 | |
| CYC 2023 MISSA Icebreaker | New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-League | 2 Divisions | Official | 14/15 |