| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| May Madness Regatta | Pewaukee Lake Sailing School | Skipper | 6/17 (B Div) | |
| MISSA Central Baker Qualifier | Lake Forest Sailing | Skipper | 10/1010/10 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Reserve | N/A | |
| Yeah Buoy! Regatta 2022 | Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Skipper | 3/13 (B Div) | |
| Banks Blackwell Invitational | Culver Academies | Skipper | 14/17 (A Div) | |
| MISSA Great Oaks Qualifier | Detroit Country Day/West Bloomfield | Reserve | N/A | |
| Kick Off Classic | Glenbrook South | Reserve | N/A |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA CENTRAL BAKER QUALIFIER | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 9/10 | |
| MISSA CENTRAL MALLORY QUALIFIER | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 12/12 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Skipper, Crew | 15/18 (A Div) | |
| Autumn Classic/Last Chance Great Lakes Champs | Chicago Yacht Club | Reserve | N/A | |
| Art Johnson | White Bear Lake | Skipper | 23/23 (A Div) | |
| Banks Blackwell - Central GLQ | Culver Academies | Reserve | N/A | |
| 2021 Fall Scramble | Pewaukee Yacht Club | Reserve | N/A | |
| Kick Off Classic | Sheridan Shore Sailing School | Skipper, Crew | 13/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Varsity In-house Zarmy #5 | Sheridan Shore Sailing School | Skipper | 3/7 | |
| Zarmy Varsity House #4 | Sheridan Shore Sailing School | Skipper | 14/19 | |
| House Varsity Zarmy #3 | Sheridan Shore Sailing School | Skipper | 7/19 | |
| Varsity Zarmy House #2 | Sheridan Shore Sailing School | Skipper | 15/19 | |
| Varsity Zarmy House #1 | Sheridan Shore Sailing School | Skipper | 17/19 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Skipper, Crew | 21/22 (A Div)21/22 (B Div) | |
| Lake Max Fall Regatta | Culver Academies | Skipper | 18/18 (B Div) |