May 14, 2023 @ 15:24:16 EDT
| Name | Host | Type | Scoring | Last race | Place(s) |
|---|---|---|---|---|---|
| May Madness Regatta | Pewaukee Lake Sailing School | Promotional | 2 Divisions | Final | 12/17 |
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Central Mallory Qualifier | Lincoln Park | League Championship | 2 Divisions | Official | 14/16 | |
| CYC 2023 MISSA Icebreaker | New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-League | 2 Divisions | Official | 13/15 |