| MISSA Great Lakes Championship | Hyman G. Rickover Na/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | | Crew | 16/20 (A Div) |
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | | Crew | 2/22 (A Div) |
| 2019 Autumn Classic | Chicago Yacht Club Belmont | | Crew | 5/13 (A Div) |
| Banks Blackwell Regatta | Culver Academies | | Skipper, Crew | 6/22 (B Div) |
| Lake Max Fall Regatta | Culver Academies | | Crew | 1/18 (A Div) |
| Red Hat Regatta | Detroit Country Day/West Bloomfield | | Skipper | 10/23 (B Div) |
| Kick Off Classic 420s | Sheridan Shore Sailing School | | Crew | 1/15 (A Div) |