| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NIT (Founders Trophy) | The Station | Reserve | N/A | |
| MISSA Silver sail-off | Chicago Yacht Club Belmont | Skipper | 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 | Skipper | 1/7 | |
| Christchurch Spring Intersectional Kick Off | Christchurch School | Skipper | 6/20 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 Rose Bowl Regatta - Silver | USC - US Sailing Center - Long Beach, CA | Skipper | 3/22 (B Div) | |
| Chicago YC Scrimmage | NASA Space Force | Skipper | 1/18 | |
| Lawrence A. White Invitational | Coast Guard Academy | Skipper | 15/20 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Central Team Race Scrimmage | Chicago Yacht Club | Skipper | 6/12 | |
| Icebreaker Regatta | Chicago Yacht Club Belmont | Skipper | 9/13 (A Div) | |
| Tier 3 Columbia JV Regatta | Fenwick/Lyons Township | Skipper | 2/14 | |
| Z Trophy March 17 | Sheridan Shore Sailing School | Skipper | 2/8 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship 2017 | Columbia Yacht Club-Chicago, IL | Skipper | 6/16 (B Div) | |
| Halloween Spectacular | Badger/Big Foot/Craig | Skipper | 8/25 (B Div) | |
| MISSA Keelboat Qualifier | New Trier HS | Crew | 4/8 | |
| Banks Blackwell Invitational | Culver Academies | Skipper | 5/16 (B Div) | |
| Fall Scramble | Arrowhead/Kettle Moraine/Oconomowoc | Skipper | 9/26 (B Div) | |
| Kick Off Classic | Sheridan Shore Sailing School | Skipper | 3/17 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MYST May Madness | Arrowhead/Oconomowoc | Skipper | 15/23 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Banks Blackwell | Culver Academies | Skipper | 23/30 (B Div) |