Jun 1, 2023 @ 15:38:27 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| National Invitational Tournament (Founders Trophy) | Indian Harbor YC | National Invitational | Team | Official | 10/10 | |
| IL State Championship | Sheridan Shore Sailing School | State Championship | 2 Divisions | Official | 5/11 | |
| Rickover Regatta | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | Promotional | 1 Division | Official | 8,9,10,12/16 | |
| MYST May Madness | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 14/23 | |
| Phebe Corckran King Memorial Regatta | Annapolis Yacht Club and Severn Sailing Association | National Invitational | 2 Divisions | Official | 13/18 | |
| MISSA Baker Qualifier | Minnetonka | District Championship | Team | Official | 6/12 | |
| MISSA Mallory Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | District Championship | 2 Divisions | Official | 9/20 | |
| MISSA Central Baker Qualifier | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | League Championship | Team | Official | 3/9 | |
| Mallory Central Qualifiers | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 1/11 | |
| MISSA Icebreaker | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | In-League | 2 Divisions | Official | 3/16 | |
| Columbia Bay Scrimmage #1 | Columbia Yacht Club-Chicago, IL | In-League | 2 Divisions | Official | 2/8 | |
| Z Trophy #1 | Sheridan Shore Sailing School | In-League | 2 Divisions | Official | 2/8 |