Nov 10, 2019 @ 16:00:09 EST
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Crew | 10/17 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Crew | 10/22 (B Div) | |
| 2019 Autumn Classic | Chicago Yacht Club Belmont | Crew | 7/13 (B Div) | |
| Banks Blackwell Regatta | Culver Academies | Crew | 2/22 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Crew | 9/13 (B Div) | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Reserve | N/A | |
| MISSA Keelboat Qualifier | Chicago Yacht Club | Crew | 11/13 |
