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| Mon | Sep 17 | U13GC | Henderson Park West | 21:00 | Bradford Eagles 2005G | 2 - 3 | SSU 2005G |
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| Tue | Sep 18 | Mens | Barrie SC Development Centre | 21:00 | Barrie FC Blazers Prem | 5 - 2 | Collingwood United Div 1 |
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| Tue | Sep 18 | Mens | Mount Albert Lions #1 | 21:00 | Mt Albert Kings (Div 1) | 2 - 2 | Alliston United Div 1 |
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| Wed | Sep 19 | O35 | Henderson Field | 21:00 | Bradford Wolves O35 | 7 - 0 | Muskoka United O35 |
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| Thu | Sep 20 | O35 | Barrie SC Development Centre | 21:00 | Barrie FC O35 | | 1857 FC O35 |
|
| Thu | Sep 20 | U13GC | Fisher Field #2 | 19:00 | Collingwood United U13G | | Barrie FC 2005G Blue |
|
| Fri | Sep 21 | O35 | Barrie SC Development Centre | 21:00 | Barrie Masters O35 | | Barrie Sons Of Pitches O35 |
|
| Sun | Sep 23 | O35 | Gostick Park #1 | 16:00 | Muskoka United O35 | | Bradford Wolves O35 |
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| Sun | Sep 23 | O35 | Innisfil Recreation Complex 2 | 11:00 | Innisfil Greyhounds O35 | | 1857 FC O35 |
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| Sun | Sep 23 | Mens | Kiwanis Park 1 - Owen Sound | 17:00 | Owen Sound Strikers | | Alliston United Div 1 |
|
| Sun | Sep 23 | Mens | Nottawasaga Inn #1 | 16:00 | Alliston Arsenal (Prem) | | Bradford District Wolves Prem |
