May 2, 2023 @ 12:46:40 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| IL State Championship | Sheridan Shore Sailing School | State Championship | 2 Divisions | Official | 2/11 | |
| ISSA Fleet Racing Championship (Mallory Trophy) | MIT Sailing Pavilion | National Championship | 2 Divisions | Official | 17/20 | |
| Rickover Regatta | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | Promotional | 1 Division | Official | 4,7,11/16 | |
| MISSA Baker Qualifier | Minnetonka | District Championship | Team | Official | 5/12 | |
| MISSA Mallory Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | District Championship | 2 Divisions | Official | 1/20 | |
| MISSA Central Baker Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | League Championship | Team | Official | 1/9 | |
| Mallory Central Qualifiers | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 2/11 | |
| MISSA Icebreaker | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | In-League | 2 Divisions | Official | 2/16 | |
| Z Trophy #1 | Sheridan Shore Sailing School | In-League | 2 Divisions | Official | 1/8 |