Nov 11, 2018 @ 18:00:27 EST
| Name | Host | Type | Scoring | Last race | Place(s) |
|---|---|---|---|---|---|
| Shepherd Championship | Columbia Sailing School | District Championship | 2 Divisions | Final | 12/13 |
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| Halloween Spectacular | Lake Forest | District Champ Qualifier | 2 Divisions | Official | 20/20 | |
| Boats n' Bingo Regatta | Columbia Sailing School | In-District | 2 Divisions | Official | 8/8 | |
| Autumn Classic Central Great Lakes Qualifier | Latin of Chicago/New Trier HS/St. Ignatius (IL)/Walter Payton Colleg | District Champ Qualifier | 2 Divisions | Official | 14/16 | |
| Lake Michigan Invite | Macatawa Bay Junior Association | Promotional | 2 Divisions | Official | 11/11 | |
| Fall Scramble | Arrowhead/Oconomowoc | Promotional | 2 Divisions | Official | 8/28 |
