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| Tue | Sep 16 | U14B | Eastview Park B | 19:00 | Barrie SC U14B | | MUFC U14B |
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| Tue | Sep 16 | O35 | Innisfil Recreation Complex 1 | 20:00 | Innisfil Greyhounds O35 | | Orillia Soccer O35 |
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| Tue | Sep 16 | U14B | West Orillia Sports Complex Grass | 19:00 | ODSC U14B | | SSU U14B |
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| Fri | Sep 19 | O35 | Henderson Field | 21:00 | Union Vintage O35 | | Bradford Wolves FC O35 |
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| Fri | Sep 19 | O35 | Innisfil Recreation Complex 1 | 21:00 | Barrie SOP O35 | | 1857 FC O35 |
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| Fri | Sep 19 | O45 | Innisfil Recreation Complex 2 | 18:30 | Barrie Packers O45 | | Orillia Inter O45 |
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| Sat | Sep 20 | U14B | G.A. Wright | 14:00 | SSU U14B | | MUFC U14B |
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| Sun | Sep 21 | O35 | Innisfil Recreation Complex 1 | 10:00 | Innisfil Greyhounds O35 | | Americas United O35 |
