Oct 27, 2019 @ 15:45:10 EDT
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Skipper | 21/22 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Great Oaks Qualifier MISSA Silver | Pontiac Yacht Club | Skipper | 11/12 | |
| Great Oaks Qualifier MISSA Red | Detroit Country Day/Groves/West Bloomfield | Skipper | 14/14 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| May Madness | Pewaukee Yacht Club | Skipper | 19/21 (A Div) | |
| B. Hill #1 | Lake Forest | Skipper | 11/13 | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/Trinity/U Chicago Laboratory/Whitney Young | Skipper | 11/14 (B Div) | |
| Z Trophy Ice Breaker #2 | Sheridan Shore Sailing School | Skipper | 4/5 | |
| Z Trophy Ice Breaker | Sheridan Shore Sailing School | Skipper | 9/10 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Lake Forest | Crew | 18/20 (B Div) | |
| MISSA Great Oaks Qualifier | New Albany/Olentangy/Olentangy Liberty/Olentangy Orange/Thomas Worthington/Westerville Central/Westerville North/Westerville South | Crew | 21/25 | |
| Banks Blackwell Invitational Regatta | Culver Academies | Crew | 10/17 (B Div) | |
| Fall Scramble | Arrowhead/Oconomowoc | Crew | 1/28 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| May Madness | Arrowhead/Oconomowoc | Crew | 8/13 (B Div) | |
| MISSA Baker Qualifier | Pontiac Yacht Club | Crew | 11/12 | |
| Tier 3 Columbia JV Regatta | Fenwick/Lyons Township | Crew | 3/14 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Z Trophy VTR Regatta | Sheridan Shore Sailing School | Crew | 2/42/42/4 | |
| Chicago YC JV Central Series #2 | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 15/26 | |
| Banks Blackwell Invitational | Culver Academies | Crew | 16/16 (B Div) | |
| MISSA Central JV Series #1 | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 24/24 |
