Nov 9, 2019 @ 18:30:07 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 | 13/17 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Kick Off Classic 420s | Sheridan Shore Sailing School | Crew | 2/15 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Skipper, Crew | 10/13 (B Div) | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 16/16 (B Div) | |
| Lake Michigan Invite | Macatawa Bay Junior Association | Skipper | 11/11 (B Div) |
