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| Tue | May 22 | U18GRC | Conroy Park | 19:00 | Huntsville Strikers U18G | 1 - 1 | SSU U18G |
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| Tue | May 22 | B12Dev | Harvie Field | 19:00 | Barrie FC U12B2 | 1 - 4 | Innisfil Stampeders U12B |
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| Tue | May 22 | U13GC | New Tecumseth Park #5 | 19:00 | SSU 2005G | 5 - 3 | Muskoka FC U13G |
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| Tue | May 22 | O45A | Nottawasaga Inn #1 | 18:30 | Alliston Wanderers O45-A | 1 - 0 | Barrie Masters O45A |
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| Wed | May 23 | U13BC | Barrie SC Development Centre | 19:00 | Barrie FC 2005B | 3 - 1 | Bradford Eagles 2005B |
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| Wed | May 23 | Mens | Cericola Arena | 21:00 | Bradford District Wolves Prem | 2 - 1 | Collingwood United Div 1 |
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| Wed | May 23 | U15BR | Fisher Field #3 | 19:00 | Collingwood United U15B | 6 - 1 | Bracebridge Storm U15B |
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| Wed | May 23 | G10Dev | Innisfil Recreation Complex 4 | 19:00 | Innisfil Stampeders U10G | 0 - 0 | SSU 2008G1 |
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| Wed | May 23 | U16GRC | Klondike Park - Wasaga Beach | 19:00 | WBSC U16G | 4 - 1 | Huntsville Strikers U16G |
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| Wed | May 23 | G12Dev | McCulley North Mini 2 | 19:15 | Huntsville Strikers U12G | 8 - 0 | Bracebridge Storm U12G |
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| Wed | May 23 | U15BR | McCulley South 1 | 19:15 | Huntsville Strikers U15B | 7 - 0 | Orillia Lightning U15B |
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| Wed | May 23 | U16GRC | Patrick Fogarty Catholic SS | 19:00 | Ramara Rockets U16G | 6 - 0 | WBSC U16G2 |
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| Wed | May 23 | U15BR | West Orillia Sports Complex Grass | 19:00 | Orillia Lightning U15B2 | 14 - 0 | SSU U15B |
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| Thu | May 24 | G10Dev | Barrie SC Trg Field | 19:00 | Barrie FC U10G | 0 - 0 | Barrie FC U9G |
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| Thu | May 24 | G10Dev | Gostick Park #4 | 19:00 | Bracebridge Storm U10G | 0 - 0 | SSU 2008G2 |
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| Thu | May 24 | G10Dev | McCulley North Mini 2 | 19:15 | Huntsville Strikers U10G | 0 - 0 | Wasaga Beach U10G |
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| Thu | May 24 | Mens | Mount Albert Lions #1 | 21:00 | Mt Albert Kings (Div 1) | 3 - 3 | Alliston Arsenal (Prem) |
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| Thu | May 24 | Mens | Nottawasaga Inn #1 | 18:30 | Alliston United Div 1 | 0 - 6 | Orillia Inter Prem |
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| Fri | May 25 | O35 | Barrie SC Development Centre | 21:00 | Barrie FC O35 | 4 - 1 | Barrie Sons Of Pitches O35 |
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| Fri | May 25 | O35 | Gostick Park #1 | 21:00 | Muskoka United O35 | 2 - 2 | 1857 FC O35 |
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| Fri | May 25 | O45B | Kitchener Park (Orillia) Field E | 18:30 | Orillia Mens Soccer O45B | 1 - 2 | Barrie Packers O45B |
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| Fri | May 25 | O45B | Klondike Park - Wasaga Beach | 19:00 | Wasaga Warriors O45B | 2 - 2 | Innisfil Greyhounds O45B |
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| Fri | May 25 | O45A | Verstraten Park | 21:00 | Barrie FC O45A | 2 - 2 | Orangeville Athletic O45A |
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| Fri | May 25 | O35 | West Orillia Sports Complex Grass | 21:00 | Orillia DSC O35 | 2 - 1 | Barrie Masters O35 |
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| Sat | May 26 | U13GC | Gostick Park #1 | 18:00 | Muskoka FC U13G | 3 - 0 | U13G North Bay Selects |
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| Sun | May 27 | Mens | Galloway Park 1 | 18:00 | Huronia Saints (Div 1) | 3 - 3 | Mt Albert Kings (Div 1) |
