| MISSA Great Lakes Championship | Hyman G. Rickover Na/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | | Reserve | N/A |
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | | Crew | 6/22 (B Div) |
| ISSA-PCISA National All Girls Invitational | San Diego Yacht Club | | Crew | 19/24 (A Div) |
| 2019 Autumn Classic | Chicago Yacht Club Belmont | | Reserve | N/A |
| Banks Blackwell Regatta | Culver Academies | | Crew | 3/22 (B Div) |
| Lake Max Fall Regatta | Culver Academies | | Crew | 14/18 (A Div) |
| MISSA Girls Great Lakes Championship | Grosse Pointe South/GPYC | | Crew | 9/10 (A Div) |
| Kick Off Classic 420s | Sheridan Shore Sailing School | | Crew | 1/15 (A Div) |