| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Crew | 12/15 (B Div) |
It appears Sarah Trunsky has not participated in any regattas this season.
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 ISSA Keelboat Invitational | Shorecrest Prep/St. Petersburg | Crew | 7/10 | |
| MISSA Great Lakes Championship | Hyman G. Rickover Na/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 15/20 (A Div) | |
| MISSA Keelboat Qualifier | Culver Academies | Crew | 2/13 | |
| Pistol Pete Classic | NASA Space Force | Crew | 13/17 | |
| Lake Max Fall Regatta | Culver Academies | Crew | 3/18 (A Div) | |
| MISSA Girls Great Lakes Championship | Grosse Pointe South/GPYC | Crew | 8/10 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NIT (Founders Trophy) | The Station | Reserve | N/A | |
| MISSA Silver sail-off | Chicago Yacht Club Belmont | Crew | 1/3 | |
| MISSA Baker Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Reserve | N/A | |
| Central Baker pre-Qualifier | Chicago Yacht Club Belmont | Crew | 1/7 | |
| Christchurch Spring Intersectional Kick Off | Christchurch School | Crew | 6/20 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 Rose Bowl Regatta - Silver | USC - US Sailing Center - Long Beach, CA | Crew | 3/22 (B Div) | |
| Chicago YC Scrimmage | NASA Space Force | Reserve | N/A | |
| Lawrence A. White Invitational | Coast Guard Academy | Crew | 15/20 (B Div) | |
| MISSA Girls' Championship | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 11/12 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Culver Spring Regatta | Culver Academies | Crew | 3/16 (A Div) | |
| Rickover Regatta | Hyman G. Rickover Na | Crew | 2/22 | |
| 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 | 13/19 | |
| Icebreaker Regatta | Chicago Yacht Club Belmont | Crew | 5/13 (B Div) | |
| Tier 3 Columbia JV Regatta | Fenwick/Lyons Township | Crew | 5/14 |