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| Tue | May 19 | U15GC | G.S. Gaston Sports Park 5 | 19:00 | SSU U15G | | Barrie Spirit U15G White |
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| Wed | May 20 | U10B | Livingstone Park B | 19:00 | Barrie Cardinals U10B Red | | Barrie Cardinals U10B Black |
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| Wed | May 20 | Mens | Wyevale Park | 20:30 | Huronia Saints | 1 - 3 | Alliston FC |
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| Thu | May 21 | U16B | Eastview Park B | 21:00 | Barrie Spirit U16B White | | Bradford Wolves U16B |
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| Fri | May 22 | O35 | Henderson Park West | 21:00 | 1857 FC O35 | 5 - 3 | Innisfil Greyhounds O35 |
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| Fri | May 22 | O35 | West Orillia Sports Complex Grass | 21:00 | Orillia Lightning O35 | 4 - 2 | Bradford Wolves O35 |
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| Sun | May 24 | Mens | Conroy Park | 19:00 | Huntsville Strikers 1 Mens | 2 - 2 | Barrie Blazers |
