May 8, 2021 @ 16:00:03 EDT
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| IL State Champs | Sheridan Shore Sailing School | Crew | 3/14 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| New Trier Regatta | New Trier HS | Crew | 11/18 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 Autumn Classic | Chicago Yacht Club Belmont | Reserve | N/A | |
| Banks Blackwell Regatta | Culver Academies | Skipper | 22/22 (B Div) | |
| Kick Off Classic Lasers | Sheridan Shore Sailing School | Skipper | 10/10 | |
| Kick Off Classic 420s | Sheridan Shore Sailing School | Crew | 12/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| B. Hill #1 | Lake Forest | Skipper | 13/13 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Skipper | 13/13 (A Div) | |
| Art Johnson | Mahtomedi/Mounds Park Academy/Mounds View/White Bear Lake | Skipper, Crew | 17/22 (A Div) | |
| Boats n' Bingo Regatta | Columbia Sailing School | Skipper | 4/8 (B Div) | |
| Banks Blackwell Invitational Regatta | Culver Academies | Skipper, Crew | 12/17 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Culver Spring Regatta | Culver Academies | Crew | 16/16 (A Div) | |
| Rickover Regatta | Hyman G. Rickover Na | Crew | 19/22 | |
| Tier 3 Chicago YC JV Regatta | Hinsdale Central/Hyman G. Rickover Na/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 16/19 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Z Trophy JV Regatta | Sheridan Shore Sailing School | Crew | 12/14 |
