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| Mon | Sep 14 | U16B | Eastview Park B | 19:00 | Barrie Spirit U16B White | 4 - 2 | North Simcoe Soccer Club U16B |
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| Mon | Sep 14 | U9B | G.S. Gaston Sports Park 1 | 18:30 | SSU U9B White | | Bradford Wolves U9B |
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| Mon | Sep 14 | U10B | Gostick Park #3B | 18:30 | MUFC U10B Blue | | Collingwood United U10B Black |
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| Mon | Sep 14 | U10B | Henderson Park 3B | 19:00 | Bradford Wolves U10B | | Wasaga Beach SC U10B |
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| Tue | Sep 15 | U15GCC | Barrie SC Development Centre | 19:00 | Barrie Spirit U15G White | 3 - 3 | Collingwood United U15G |
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| Tue | Sep 15 | U12G | Golden Meadows Park | 18:00 | Barrie Spirit U12G White | | Orillia Lightning U12G |
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| Tue | Sep 15 | U10B | Henderson Park 3C | 18:30 | Bradford Wolves U10B White | | Barrie Spirit U10B Gold |
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| Wed | Sep 16 | Mens | Eastview Park B | 21:00 | Barrie Blazers | 0 - 2 | Alliston FC |
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| Wed | Sep 16 | U12G | Fisher Field #4 | 18:30 | Collingwood United U12G Black | | Barrie Spirit U12G White |
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| Wed | Sep 16 | U16B | West Orillia Sports Complex Grass | 19:00 | Orillia Soccer U16B | | Innisfil Soccer U16B |
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| Wed | Sep 16 | Mens | West Orillia Sports Complex Grass | 21:00 | Orillia Inter | 8 - 0 | Huntsville Strikers 2 Mens |
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| Wed | Sep 16 | U12G | West Orillia Sports Complex Mini 1 | 18:00 | Orillia Lightning U12G | | Collingwood United U12G Red |
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| Thu | Sep 17 | U13B | G.S. Gaston Sports Park A | 18:00 | SSU U13B | | Collingwood United U13 Boys |
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| Thu | Sep 17 | O35 | Henderson Park East | 20:00 | Bradford Wolves O35 | | Innisfil Greyhounds O35 |
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| Thu | Sep 17 | U16B | Henderson Park West | 19:00 | Bradford Wolves U16B | | North Simcoe Soccer Club U16B |
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| Thu | Sep 17 | U10G | Huronia North B | 18:00 | Barrie Spirit U10G White | | Collingwood United U10G Red |
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| Thu | Sep 17 | O45 | Innisfil Recreation Complex 3 | 21:00 | Barrie Masters O45 | | Innisfil Greyhounds O45 |
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| Thu | Sep 17 | O45 | Nottawasaga Inn #1 | 17:45 | Nottawasaga FC O45 | | Barrie Packers O45 |
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| Fri | Sep 18 | Mens | West Orillia Sports Complex Grass | 21:00 | Orillia Inter | | Alliston United |
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| Sun | Sep 20 | Mens | Conroy Park | 17:00 | Huntsville Strikers 2 Mens | | Orillia Inter |
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| Sun | Sep 20 | O35 | Innisfil Recreation Complex 3 | 10:00 | Innisfil Greyhounds O35 | | 1857 FC O35 |
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| Sun | Sep 20 | Mens | Nottawasaga Inn #1 | 16:00 | Alliston United | | Huntsville Strikers 1 Mens |
