May 18, 2019 @ 08:08:39 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| May Madness | Pewaukee Yacht Club | Promotional | 2 Divisions | Official | 20/21 | |
| B. Hill #1 | Lake Forest | Promotional | 1 Division | Official | 11,12/13 | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/Trinity/U Chicago Laboratory/Whitney Young | League Championship | 2 Divisions | Official | 13/14 | |
| Z Trophy Ice Breaker #2 | Sheridan Shore Sailing School | In-District | 1 Division | Official | 4/5 | |
| Z Trophy Ice Breaker | Sheridan Shore Sailing School | In-League | 1 Division | Official | 9/10 |
