| Shepherd Championship | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | State Championship | 4 Divisions | | Pending | 2/15 |
| Monster Mash | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-League | Team | | Pending | 5/8 |
| Sunday's with Scouts 2 | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Promotional | Combined | | Pending | 1,4/9 |
| Sunday’s with Scouts | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Promotional | Combined | | Official | 1,8/8 |
| Sunday | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | Promotional | 2 Divisions | | Official | 1,3/9 |
| Historic Pandemic Team Race Classic | Chicago Yacht Club Belmont | In-District | Team | | Official | 5/10 |
| Banks Blackwell Invitational | Culver Academies | In-District | 2 Divisions | | Official | 2,3/9 |
| Sunday Races | Fenwick/Jones College Prep/Lane Tech College Pr/Lyons Township/U Chicago Laboratory/Whitney Young | In-League | 2 Divisions | | Official | 1,6,11/11 |