Sep 23, 2021 @ 09:59:16 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | District Championship | 2 Divisions | Official | 14/17 | |
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | District Champ Qualifier | 2 Divisions | Official | 17/22 | |
| Boats n' Bingo Regatta | Lyons Township/U Chicago Laboratory/Whitney Young | Promotional | 1 Division | Official | 4,10/12 | |
| 2019 Autumn Classic | Chicago Yacht Club Belmont | League Championship | 2 Divisions | Official | 13/13 | |
| Banks Blackwell Regatta | Culver Academies | In-District | 2 Divisions | Official | 12,17/22 | |
| 2019 MYST Fall Scramble | PLSS/MYST | Promotional | 2 Divisions | Official | 27/30 | |
| Kick Off Classic 420s | Sheridan Shore Sailing School | In-District | 2 Divisions | Official | 10/15 |
