May 21, 2023 @ 20:16:43 EDT
| Name | Host | Type | Scoring | Last race | Place(s) |
|---|---|---|---|---|---|
| National Invitational Tournament (Founders Trophy) | Lake Massapoag YC | National Invitational | Team | Final | 10/10 |
| 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 | 6/8 | |
| Scrappy Memorial Regatta | Culver Academies | In-District | Combined | Official | 3,7/8 | |
| 2023 May 6 Regatta @ Sheridan Shore | Sheridan Shore | In-District | 1 Division | Official | 14,15/16 | |
| MISSA Baker Qualifier | Lake Forest Sailing | District Championship | Team | Official | 3/10 | |
| 2023 MISSA Mallory Qualifier | Lake Forest Sailing | District Championship | 2 Divisions | Official | 16/20 | |
| Saturday 22 @ CYC Regatta | Chicago Yacht Club - Belmont | In-League | 1 Division | Official | 5,6,8,18/21 | |
| MISSA Central Baker Qualifier | Lake Forest Sailing | District Champ Qualifier | Team | Official | 3/10 | |
| 2023 Spring April 15 JV Regatta | Sheridan Shore | In-District | 1 Division | Official | 4,8,12/13 | |
| Central Mallory Qualifier | Lincoln Park | League Championship | 2 Divisions | Official | 10/16 | |
| Columbia Tier 3 | Columbia YC | In-League | Combined | Official | 6/9 | |
| CYC 2023 MISSA Icebreaker | New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-League | 2 Divisions | Official | 8,11/15 |