| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Shepherd Championship | Jones College Prep/Lane Tech College Pr/Lincoln Park/Oak Park River/Whitney Young | Skipper | 15/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Great Lakes Last Chance Qualifier | Jones College Prep/Lane Tech College Pr/Lincoln Park/Oak Park River/Whitney Young | Skipper | 8/9 (A Div) | |
| Columbia Tier 3 | Jones College Prep/Lane Tech College Pr/Lincoln Park/Whitney Young | Skipper | 8/18 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MISSA Central GLC Quals | Lake Forest | Skipper | 13/14 (A Div) | |
| Fall Scramble Regatta | Pewaukee Yacht Club | Skipper | 18/21 (A Div) | |
| 2023 Kick Off Classic | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | Skipper | 13/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Open Great Lakes Qualifier | Culver Academies | Skipper | 10/10 (A Div) | |
| Dusty Waters Regatta | Arrowhead/Kettle Moraine/Marquette/Oconomowoc/Pewaukee | Skipper | 16/20 (A Div) | |
| Kick Off Classic | Glenbrook South | Skipper | 16/17 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Autumn Classic/Last Chance Great Lakes Champs | Chicago Yacht Club | Skipper | 15/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Skipper | 13/15 (B Div) | |
| Sunday Races | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Skipper | 8/11 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Crew | 5/17 (A Div) | |
| Halloween Spectacular | Glenbrook South/Lake Forest Academy/Lake Forest/Stevenson | Skipper | 13/22 (B Div) | |
| 2019 Autumn Classic | Chicago Yacht Club Belmont | Skipper | 11/13 (B Div) | |
| Missa Great Oaks Gold* Qualifier | Pontiac Yacht Club | Skipper, Crew | 16/1616/16 | |
| Great Oaks Qualifier- MISSA Green | Detroit Country Day/Groves/West Bloomfield | Crew | 7/14 | |
| 2019 MYST Fall Scramble | PLSS/MYST | Skipper | 8/30 (B Div) | |
| Kick Off Classic 420s | Sheridan Shore Sailing School | Crew | 5/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | Skipper | 12/13 (B Div) | |
| Halloween Spectacular | Lake Forest | Skipper | 16/20 (B Div) | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Skipper | 15/16 (B Div) | |
| Banks Blackwell Invitational Regatta | Culver Academies | Skipper | 15/17 (A Div) | |
| Fall Scramble | Arrowhead/Oconomowoc | Skipper | 9/28 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Central Team Race Scrimmage | Chicago Yacht Club | Crew | 11/12 | |
| Mallory Central Qualifier | Brother Rice (IL)/Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory | Crew | 1/13 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Shepherd Championship 2017 | Columbia Yacht Club-Chicago, IL | Crew | 1/16 (A Div) | |
| Halloween Spectacular | Badger/Big Foot/Craig | Crew | 12/25 (A Div)18/25 (B Div) | |
| MISSA Autumn Classic | Hinsdale Central/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Reserve | N/A | |
| Fall Scramble | Arrowhead/Kettle Moraine/Oconomowoc | Crew | 22/26 (B Div) | |
| Kick Off Classic | Sheridan Shore Sailing School | Crew | 17/17 (A Div) |