| Name | Host | Type | Scoring | Start time |
|---|---|---|---|---|
| 2019 Autumn Classic | Chicago Yacht Club Belmont | League Championship | 2 Divisions | 10/12/2019 @ 10:00 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Great Oaks Qualifier MISSA Silver | Pontiac Yacht Club | Crew | 11/12 | |
| Great Oaks Qualifier MISSA Red | Detroit Country Day/Groves/West Bloomfield | Reserve | N/A |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| May Madness | Pewaukee Yacht Club | Crew | 19/21 (A Div) | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/Trinity/U Chicago Laboratory/Whitney Young | Crew | 11/14 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Boats n' Bingo Regatta | Columbia Sailing School | Crew | 5/8 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Culver Spring Regatta | Culver Academies | Crew | 14/16 (A Div) | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory | Crew | 8/13 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Chicago YC JV Central Series #2 | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 19/26 | |
| Banks Blackwell Invitational | Culver Academies | Skipper | 16/16 (B Div) | |
| MISSA Central JV Series #1 | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 24/24 | |
| Fall Scramble | Arrowhead/Kettle Moraine/Oconomowoc | Crew | 20/26 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| IL State Championship | Sheridan Shore Sailing School | Crew | 7/11 (B Div) | |
| MYST May Madness | Arrowhead/Oconomowoc | Crew | 22/23 (B Div) | |
| Mallory Central Qualifiers | Lake Forest | Crew | 9/11 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship 2016 | Columbia Yacht Club-Chicago, IL | Crew | 3/17 (A Div) | |
| Halloween Spectacular | Lake Forest | Crew | 22/25 (A Div) | |
| Banks Blackwell | Culver Academies | Crew | 18/30 (A Div) |