Nov 10, 2019 @ 15:15:09 EST
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Great Lakes Championship | Hyman G. Rickover Na/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 19/20 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Skipper | 19/22 (B Div) | |
| Art Johnson Memorial Regatta | White Bear Sailing School | Skipper | 9/24 (B Div) | |
| Banks Blackwell Regatta | Culver Academies | Skipper | 21/22 (A Div) | |
| Kick Off Classic 420s | Sheridan Shore Sailing School | Skipper | 11/15 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| B. Hill #1 | Lake Forest | Crew | 13/13 |
