| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Great Lakes Championship | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 17/20 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Lake Forest | Skipper | 3/20 (A Div) | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 10/16 (A Div) | |
| Fall Scramble | Arrowhead/Oconomowoc | Skipper | 12/28 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Mallory Qualifier | Arrowhead | Skipper | 16/20 (B Div) | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory | Skipper | 5/13 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Badger/Big Foot/Craig | Skipper | 20/25 (A Div) | |
| MISSA Autumn Classic | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Crew | 10/17 (B Div) | |
| MISSA Great Oaks (Z-420 Qualifying) | Benilde St Margarets/Chanhassen/Orono/Providence Academy/Wayzata | Crew | 5/11 | |
| MISSA Great Oaks - Championship Fleet | Benilde St Margarets/Chanhassen/Orono/Providence Academy/Wayzata | Skipper, Crew | 11/1411/14 | |
| Banks Blackwell Invitational | Culver Academies | Crew | 7/16 (A Div) | |
| MISSA Cressy Radial Qualifier | Sheridan Shore Sailing School | Skipper | 19/25 | |
| Kick Off Classic | Sheridan Shore Sailing School | Skipper | 12/17 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MYST May Madness | Arrowhead/Oconomowoc | Skipper | 9/23 (B Div) | |
| Columbia Bay Scrimmage #1 | Columbia Yacht Club-Chicago, IL | Skipper | 5/8 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship 2016 | Columbia Yacht Club-Chicago, IL | Skipper | 11/17 (B Div) | |
| Halloween Spectacular | Lake Forest | Skipper | 18/25 (B Div) | |
| Banks Blackwell | Culver Academies | Skipper | 14/30 (B Div) | |
| MISSA Autumn Classic | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius College/Walter Payton Colleg | Crew | 19/19 (A Div) | |
| Pewaukee Fall Scramble | Pewaukee Yacht Club | Crew | 19/23 (A Div) | |
| Kick Off Classic 2016 420's | Sheridan Shore Sailing School | Crew | 14/17 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Halloween Spectacular | Lake Forest Sailing | Crew | 23/24 (A Div) | |
| Great Oaks Qualifier - Silver | Lake Forest | Crew | 12/12 | |
| Great Oak Qual Group B | Lake Forest Sailing | Crew | 14/14 | |
| Pewaukee Fall Scramble | Pewaukee Yacht Club | Crew | 23/23 (A Div) |