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| Tue | May 21 | U18GR | Patrick Fogarty Catholic SS | 19:00 | Ramara Rockets U18G | 10 - 0 | Huntsville Strikers U16G |
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| Wed | May 22 | U13BC | Barrie Sports Complex #5 | 19:00 | Barrie U13B White | 1 - 6 | Innisfil Stampeders U13B |
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| Wed | May 22 | U14 GC | Eastview Park B | 19:00 | Barrie U14G White | 8 - 0 | Innisfil Stampeders U14G |
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| Wed | May 22 | O35 | Eastview Park B | 21:00 | Barrie FC O35 SOP | 1 - 2 | Orillia Lightning O35 |
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| Wed | May 22 | O45A | Georgian College Turf | 21:00 | Barrie Masters O45A | 0 - 2 | Alliston Wanderers O45A |
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| Wed | May 22 | U13BC | Graham Soccer Field | 19:00 | North Bay Selects SC U13B | 0 - 7 | GSSC Impact U13B |
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| Wed | May 22 | Mens | Henderson Field | 21:00 | Bradford Eagles Men | 2 - 0 | Owen Sound Strikers |
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| Wed | May 22 | O35 | Henderson Park East | 21:00 | Bradford Wolves O35 | | Muskoka United O35 |
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| Wed | May 22 | U14 GC | James Jerome | 18:00 | GSSC Impact U14G | 2 - 0 | North Bay Lakers U14G |
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| Wed | May 22 | U13BC | West Orillia Sports Complex Grass | 19:00 | Orillia Lightning U13B | 0 - 3 | Bradford Eagles U13B |
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| Thu | May 23 | U16BC | Fisher Field #2 | 19:30 | Collingwood United U16B | | Innisfil Stampeders U16B |
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| Thu | May 23 | B11Dev | Gostick Park #3B | 19:15 | Bracebridge Storm U11B | | Bradford Eagles U11B |
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| Thu | May 23 | B11Dev | McCulley North Mini 1 | 19:15 | Huntsville Strikers U11B | | Orillia Lightning U11B |
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| Thu | May 23 | Mens | Mt. Albert Lions Club #4 | 21:00 | Mt Albert Kings | | Barrie Blazers |
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| Fri | May 24 | O45A | Eastview Park B | 20:00 | Barrie FC O45A | | Orangeville Town O45A |
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| Fri | May 24 | O35 | Georgian College Turf | 21:00 | Barrie Masters O35 | | Huronia Saints O35 |
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| Fri | May 24 | O35 | Henderson Field | 21:00 | Bradford 1857 FC O35 | | Barrie FC O35 |
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| Fri | May 24 | O45A | Innisfil Recreation Complex 1 | 19:00 | Innisfil Greyhounds O45B | | Wasaga Warriors O45B |
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| Fri | May 24 | O45A | Kitchener Park (Orillia) Field E | 18:30 | Orillia Mens Soccer O45B | | Barrie Packers O45B |
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| Sun | May 26 | O35 | Innisfil Recreation Complex 1 | 10:00 | Innisfil Greyhounds O35 | | Muskoka United O35 |
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| Sun | May 26 | Mens | Kiwanis Park 1 - Owen Sound | 20:30 | Owen Sound Strikers | | Alliston United |
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| Sun | May 26 | U13BC | McCulley South 2 | 19:00 | Huntsville Strikers U13B | | SSU 2006B |
