| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 Autumn Classic | Chicago Yacht Club Belmont | Reserve | N/A |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Kick Off Classic 420s | Sheridan Shore Sailing School | Skipper | 2/15 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| May Madness | Pewaukee Yacht Club | Skipper | 14/21 (B Div) | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/Trinity/U Chicago Laboratory/Whitney Young | Skipper | 13/14 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Skipper | 10/13 (B Div) | |
| Halloween Spectacular | Lake Forest | Skipper | 20/20 (B Div) | |
| Lake Michigan Invite | Macatawa Bay Junior Association | Skipper | 11/11 (A Div) | |
| Fall Scramble | Arrowhead/Oconomowoc | Skipper | 21/28 (B Div) |