| ISSA Cressy Singlehanded National's IlCA 6 | Saint Thomas Aquinas | National Championship | Singlehanded | | Official | 5/18 |
| ISSA Cressy Singlehanded Nationals ILCA 7 | Saint Thomas Aquinas | National Championship | Singlehanded | | Official | 2/18 |
| Great Lakes Championships | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Championship | 2 Divisions | | Pending | 2/20 |
| Autumn Classic/Last Chance Great Lakes Champs | Chicago Yacht Club | In-District | 2 Divisions | | Official | 1/15 |
| PCISA/ISSA Girl's National Invitational | Mission Bay Yacht Club | National Invitational | 2 Divisions | | Official | 14/21 |
| Banks Blackwell - Central GLQ | Culver Academies | District Champ Qualifier | 2 Divisions | | Official | 10/16 |
| MISSA Keelboat Finals - Gold Fleet | North (WI) | Promotional | 1 Division | | Pending | 8/8 |
| Tier 3 Regatta - Oct. 2 | Chicago Yacht Club | In-League | 1 Division | | Official | 11,14/21 |
| MISSA Keelboat Quals Group A | North (WI) | District Champ Qualifier | 1 Division | | Pending | 2/8 |
| MISSA Girls Qualifier | Lake Minnetonka Sailing School | District Champ Qualifier | 2 Divisions | | Official | 6/10 |
| 2021 Fall Scramble | Pewaukee Yacht Club | Promotional | 2 Divisions | | Official | 12/26 |
| MISSA Cressy Qualifier (ILCA 7/ Full Rig) | Lake Forest Sailing | District Championship | Singlehanded | | Official | 1/18 |
| MISSA Cressy Qualifier (ILCA 6/ Radial) | Lake Forest Sailing | District Championship | Singlehanded | | Official | 2,7/36 |
| Chicago Regatta - Tier 3 | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | In-District | 1 Division | | Official | 13,15/15 |