May 23, 2021 @ 14:34:06 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Latin School of Chicago Regatta | Chicago Yacht Club | Promotional | 2 Divisions | Official | 9/17 | |
| Zarmy In-House Regatta Sunday | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | In-League | 1 Division | Official | 2,4,8,9/9 | |
| Zarmy In-House Regatta Saturday | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | In-League | 1 Division | Official | 1,2,3,5,8/8 | |
| IL State Champs | Sheridan Shore Sailing School | State Championship | 2 Divisions | Official | 8/14 | |
| Varsity In-house Zarmy | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | In-League | 1 Division | Official | 3,4,5,9,11/11 | |
| New Trier Regatta | New Trier HS | Promotional | 2 Divisions | Official | 12/18 | |
| In-House SSSS #2 | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | In-District | 1 Division | Official | 2,7,9/9 | |
| Zarmy Regatta 1 | Beacon Academy/Evanston Township HS/Glenbrook South/Loyola Academy | In-District | 1 Division | Official | 1,2,5,6,7/9 | |
| MISSA Mallory Central Qualifier | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 9/14 | |
| MISSA Central Baker Qualifier | Chicago Yacht Club | League Championship | Team | Official | 5/9 |
