| 10/3/2009 | 1:00 PM | DHALIWAL SP | 2 | Mequon United Red | 3 | Appleton Soccer Club Celtics | 1 | |
| 10/4/2009 | 12:00 PM | MERTON SP | 4 | Lake Country United U-14 Red | 1 | FC United '96 - PVYSC | 5 | |
| 10/11/2009 | 1:00 PM | USA | 1 | Appleton Soccer Club Celtics | 1 | Croatian Eagles Red | 1 | |
| 10/11/2009 | 1:30 PM | MERTON SP | 4 | Lake Country United U-14 Red | 0 | FC Milwaukee 14B Blue | 4 | |
| 10/18/2009 | 3:00 PM | USA | 1 | Appleton Soccer Club Celtics | 2 | FC United '96 - PVYSC | 1 | |
| 10/24/2009 | 1:00 PM | USA | 1 | Appleton Soccer Club Celtics | 0 | Bavarian Juniors Blue | 4 | |
| 10/24/2009 | 2:30 PM | MERTON SP | 4 | Lake Country United U-14 Red | 0 | Mequon United Red | 6 | |
| 10/25/2009 | 2:30 PM | MERTON SP | 4 | Lake Country United U-14 Red | 0 | Appleton Soccer Club Celtics | 3 | |
| 10/31/2009 | 2:00 PM | WES | 19 | SCWaukesha U14 Boys Blue | 9 | Lake Country United U-14 Red | 1 | |
| 11/1/2009 | 10:30 AM | MERTON SP | 4 | Lake Country United U-14 Red | 0 | Bavarian Juniors Blue | 4 | |
| 11/1/2009 | 1:00 PM | USA | 1 | Appleton Soccer Club Celtics | 1 | FC Milwaukee 14B Blue | 4 | |
| 11/7/2009 | 10:00 AM | CROATIAN PARK | | Croatian Eagles Red | 6 | Lake Country United U-14 Red | 0 | |
| 11/7/2009 | 2:00 PM | WES | 19 | SCWaukesha U14 Boys Blue | 6 | Appleton Soccer Club Celtics | 3 | |