Oct 27, 2019 @ 09:30:07 EDT
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Crew | 10/22 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 MYST Fall Scramble | PLSS/MYST | Crew | 19/30 (A Div) | |
| Kick Off Classic 420s | Sheridan Shore Sailing School | Crew | 14/15 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Crew | 12/13 (B Div) | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 15/16 (B Div) | |
| Fall Scramble | Arrowhead/Oconomowoc | Crew | 9/28 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Badger/Big Foot/Craig | Crew | 18/25 (B Div) |
