May 14, 2023 @ 11:00:04 EDT
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Scrappy Memorial Regatta | Culver Academies | Crew | 2/8 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2023 MISSA Mallory Qualifier | Lake Forest Sailing | Crew | 14/20 (B Div) | |
| MISSA Central Baker Qualifier | Lake Forest Sailing | Crew | 3/10 | |
| Central Mallory Qualifier | Lincoln Park | Crew | 10/16 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2023 Rose Bowl Regatta - HS Silver | Ernest J. McBride | Crew | 19/26 (B Div) | |
| MISSA Great Lakes Championship | Chicago Yacht Club | Crew | 8/20 (B Div) | |
| Open Great Lakes Qualifier | Culver Academies | Crew | 3/10 (B Div) | |
| Yeah Buoy! Regatta 2022 | Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Crew | 1/13 (B Div) | |
| MISSA Keelboat Championship | Culver Academies | Crew | 12/13 | |
| Kick Off Classic | Glenbrook South | Crew | 14/17 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2022 Phebe King Memorial Trophy Regatta | Youth Sailing Virginia | Crew | 17/17 (B Div) | |
| IL State Championships | Beacon Academy/Evanston Township HS/Loyola Academy | Crew | 7/13 (B Div) | |
| MISSA CENTRAL BAKER QUALIFIER | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 6/10 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| BRONZE - Rose Bowl 2022 | Ernest J. McBride | Crew | N/A | |
| SILVER - Rose Bowl 2022 | Ernest J. McBride | Crew | 23/32 (B Div) | |
| Banks Blackwell - Central GLQ | Culver Academies | Crew | 12/16 (A Div) | |
| Chicago Regatta - Tier 3 | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 3/15 |