Jun 1, 2023 @ 15:38:29 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Great Lakes Championship | Chicago Yacht Club | District Championship | 2 Divisions | Official | 18/20 | |
| Halloween Spectacular | Lake Forest Sailing | In-District | 2 Divisions | Official | 11/24 | |
| Dusty Water Invitational | Pewaukee Yacht Club | In-District | 2 Divisions | Official | 16/20 | |
| High School Keelboat Invite | Hinsdale Central/New Trier HS/St. Ignatius College | In-District | 1 Division | Official | 4/6 | |
| Great Oaks Qual Championship | Lake Forest | Promotional | 1 Division | Official | 11/16 | |
| Great Oak Qual Group B | Lake Forest Sailing | District Championship | 1 Division | Official | 7/14 | |
| Pewaukee Fall Scramble | Pewaukee Yacht Club | In-District | 2 Divisions | Official | 9/23 | |
| Cherryland Invitational | Grand Traverse Yacht Club | District Championship | 2 Divisions | Official | 6/10 | |
| Kick Off Classic | Sheridan Shore Sailing School | District Championship | 2 Divisions | Official | 11/20 |