| Lake Forest Fall Scramble | Lake Forest Parks and Recreation Sailing | Promotional | 1 Division | | Official | 6/15 |
| Northwest Great Lakes Qualifier | North (WI) | District Champ Qualifier | 2 Divisions | | Official | 2/7 |
| Dusty Waters Regatta_C420 | Nagawicka Lake Yacht Club | Promotional | 2 Divisions | | Official | 6/16 |
| MISSA SW Great Lakes Qualifier | Sheridan Shore Sailing School | District Champ Qualifier | 2 Divisions | | Official | 6/13 |
| CYC Fall Clinic + Tier 3 | DePaul College Prep/Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | Promotional | 1 Division | | Official | 2,3,4,12/13 |
| 2025 Kick-Off Classic | Sheridan Shore Sailing School | In-District | 2 Divisions | | Official | 11/17 |