| 8/30/2009 | 12:30 PM | UIHLEIN SP | | Milwaukee Kickers Shorewood Shadows | 1 | Milwaukee Sport Club | 0 | |
| 9/13/2009 | 3:00 PM | QUIT QUI OC | | PYSA Pumas | 1 | Sheboygan County United Strikers | 7 | |
| 9/26/2009 | 2:00 PM | HORACE MANN | 2 | Sheboygan County United Strikers | 2 | Milwaukee Kickers Shorewood Shadows | 1 | |
| 9/27/2009 | 12:00 PM | MILWAUKEE SPORTS CLUB | 3 | Milwaukee Sport Club | 1 | Milwaukee Kickers Shorewood Shadows | 0 | |
| 10/4/2009 | 4:30 PM | HALES CORNERS | 2 | United Serbian SC | 2 | Milwaukee Kickers Shorewood Shadows | 2 | |
| 10/7/2009 | 5:30 PM | HALES CORNERS | 2 | United Serbian SC | 1 | Milwaukee Kickers Shorewood Shadows | 1 | |
| 10/7/2009 | 6:00 PM | HORACE MANN | 3 | Sheboygan County United Strikers | 1 | PYSA Pumas | 0 | |
| 10/21/2009 | 5:00 AM | UIHLEIN SP | | Milwaukee Kickers Shorewood Shadows | 1 | PYSA Pumas | 0 | Yes |
| 10/21/2009 | 5:30 PM | HORACE MANN | 3 | Sheboygan County United Strikers | 4 | Milwaukee Sport Club | 2 | |
| 10/25/2009 | 11:00 AM | QUIT QUI OC | | PYSA Pumas | 0 | Milwaukee Kickers Shorewood Shadows | 3 | |
| 10/25/2009 | 3:45 PM | HALES CORNERS | 2 | United Serbian SC | 1 | Sheboygan County United Strikers | 1 | |
| 10/31/2009 | 1:30 PM | MILWAUKEE SPORTS CLUB | 3 | Milwaukee Sport Club | 0 | Sheboygan County United Strikers | 1 | |
| 11/1/2009 | 2:00 PM | UIHLEIN SP | | Milwaukee Kickers Shorewood Shadows | 4 | Sheboygan County United Strikers | 1 | |
| 11/7/2009 | 2:00 PM | HORACE MANN | 3 | Sheboygan County United Strikers | 2 | United Serbian SC | 2 | |