Jun 1, 2023 @ 15:38:11 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| LMSS Team Race VARSITY | Minnetonka | Promotional | Team | Official | 6/8 | |
| IL State Championship | Sheridan Shore Sailing School | State Championship | 2 Divisions | Official | 6/11 | |
| MYST May Madness | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 8,20/23 | |
| MISSA Mallory Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | District Championship | 2 Divisions | Official | 16/20 | |
| MISSA Central Baker Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | League Championship | Team | Official | 7/9 | |
| Mallory Central Qualifiers | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 4/11 | |
| MISSA Icebreaker | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | In-League | 2 Divisions | Official | 10/16 | |
| Columbia Bay Scrimmage #1 | Columbia Yacht Club-Chicago, IL | In-League | 2 Divisions | Official | 3,8/8 | |
| Z Trophy #1 | Sheridan Shore Sailing School | In-League | 2 Divisions | Official | 6/8 |