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| Mon | Jul 16 | U9BC | Barrie SC Trg Field | 19:00 | Barrie FC U9B2 | | Innisfil Stampeders U9B |
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| Mon | Jul 16 | U9BC | Fisher Field #8 | 19:00 | Collingwood United U9B | | Barrie FC U9B1 |
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| Mon | Jul 16 | B10Dev | Huronia North I | 18:30 | Barrie FC U10B1 | | Huntsville Strikers U10B |
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| Mon | Jul 16 | B10Dev | Huronia North I | 19:30 | Barrie FC U10B2 | | Orillia Lightning U10B |
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| Mon | Jul 16 | B10Dev | Innisfil Recreation Complex 4 | 19:00 | Innisfil Stampeders U10B | | Wasaga Beach U10B |
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| Mon | Jul 16 | U9BC | Kitchener Park (Orillia) Field C | 19:00 | Orillia Lightning U9B Team 1 | | Bracebridge Storm U9B |
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| Mon | Jul 16 | U9BC | Klondike Park D - Wasaga Beach | 19:00 | Wasaga Beach U9B | 0 - 0 | SSU 2009B |
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| Tue | Jul 17 | Mens | Barrie SC Development Centre | 21:00 | Barrie FC Blazers Prem | 4 - 2 | Alliston United Div 1 |
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| Tue | Jul 17 | G12Dev | Fisher Field #6 | 19:00 | Collingwood United U12G -White | | Collingwood United U12 Girls-Red |
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| Tue | Jul 17 | U18GRC | G.S. Gaston Sports Park 4 | 19:00 | SSU U18G | 3 - 2 | WBSC U18G |
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| Tue | Jul 17 | B11Dev | Gostick Park #3 | 19:00 | Bracebridge Storm U11B | | Orillia Lightning U11B |
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| Tue | Jul 17 | B12Dev | Harvie Field | 19:00 | Barrie FC U12B2 | | Orillia Lightning U12B |
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| Tue | Jul 17 | U13GC | Innisfil Recreation Complex 1 | 19:00 | Innisfil Stampeders U13G | 0 - 17 | Barrie FC 2005G Blue |
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| Tue | Jul 17 | B12Dev | Nantyr Park | 19:00 | Innisfil Stampeders U12B | | Wasaga Beach U12B |
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| Tue | Jul 17 | U18GRC | Tree Nursery #5 Barrie | 19:00 | Huronia Saints U18G | 4 - 0 | Huntsville Strikers U18G |
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| Tue | Jul 17 | U13GC | Verstraten Park | 19:00 | Barrie FC U13G White | 2 - 2 | Muskoka FC U13G |
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| Tue | Jul 17 | B11Dev | West Orillia Sports Complex Mini 1 | 19:00 | Orillia Lightning U11B Team 2 | | Collingwood United U11B |
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| Wed | Jul 18 | U13BC | Barrie SC Development Centre | 21:00 | Barrie FC 2005B | 11 - 0 | Wasaga Beach United |
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| Wed | Jul 18 | Mens | Fisher Field #2 | 21:00 | Collingwood United Div 1 | 5 - 1 | Bradford District Wolves Prem |
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| Wed | Jul 18 | U15BR | Fisher Field #3 | 19:00 | Collingwood United U15B | 1 - 1 | Orillia Lightning U15B2 |
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| Wed | Jul 18 | U15BR | Gostick Park #1 | 19:00 | Bracebridge Storm U15B | 2 - 3 | Huntsville Strikers U15B |
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| Wed | Jul 18 | G12Dev | Harvie Field | 19:00 | Barrie FC U12G1 | | Bracebridge Storm U12G |
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| Wed | Jul 18 | U10GC | Innisfil Recreation Complex 4 | 19:00 | Innisfil Stampeders U10G | 0 - 0 | Bracebridge Storm U10G |
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| Wed | Jul 18 | U16GRC | Klondike Park - Wasaga Beach | 19:00 | WBSC U16G2 | 0 - 4 | WBSC U16G |
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| Wed | Jul 18 | U16GRC | McCulley South 1 | 19:15 | Huntsville Strikers U16G | 0 - 2 | Ramara Rockets U16G |
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| Wed | Jul 18 | G12Dev | Nantyr Park | 19:00 | Innisfil Stampeders U12G | | Barrie FC U12G2 |
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| Wed | Jul 18 | O45A | Verstraten Park | 21:00 | Barrie Masters O45A | 1 - 3 | Alliston Wanderers O45-A |
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| Wed | Jul 18 | U15BR | West Orillia Sports Complex Grass | 19:00 | Orillia Lightning U15B | 17 - 0 | SSU U15B |
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| Thu | Jul 19 | U10GC | G.S. Gaston Sports Park C | 19:00 | SSU 2008G1 | | Barrie FC U10G |
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| Thu | Jul 19 | B12Dev | Gostick Park #3B | 19:00 | Bracebridge Storm U12B | | Huntsville Strikers U12B |
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| Thu | Jul 19 | U15BR | Kitchener Park (Orillia) Field E | 19:00 | Orillia Lightning U15B2 | | Bracebridge Storm U15B |
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| Thu | Jul 19 | Mens | Kiwanis Park 1 - Owen Sound | 21:00 | Owen Sound Strikers | | Barrie FC Blazers Prem |
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| Thu | Jul 19 | U10GC | Klondike Park D - Wasaga Beach | 19:00 | Wasaga Beach U10G | 0 - 0 | Barrie FC U9G |
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| Thu | Jul 19 | U10GC | McCulley North Mini 2 | 19:15 | Huntsville Strikers U10G | | SSU 2008G2 |
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| Thu | Jul 19 | U11BC | McCulley North Practice | 19:15 | Huntsville Strikers U11B | 0 - 0 | Orillia Lightning U11B |
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| Thu | Jul 19 | Mens | Mount Albert Lions #1 | 21:00 | Mt Albert Kings (Div 1) | 5 - 2 | Huronia Saints (Div 1) |
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| Thu | Jul 19 | U13GC | Verstraten Park | 19:00 | Barrie FC 2005G Blue | 10 - 0 | Barrie FC U13G White |
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| Fri | Jul 20 | O35 | Barrie SC Development Centre | 21:00 | Barrie FC O35 | | Bradford Wolves O35 |
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| Fri | Jul 20 | O35 | Henderson Field | 21:00 | 1857 FC O35 | | Barrie Sons Of Pitches O35 |
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| Fri | Jul 20 | O45B | Innisfil Recreation Complex 1 | 19:00 | Barrie Packers O45B | | Orillia Mens Soccer O45B |
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| Fri | Jul 20 | O45B | Innisfil Recreation Complex 2 | 20:00 | Innisfil Greyhounds O45B | | Wasaga Warriors O45B |
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| Fri | Jul 20 | O45A | Rotary Park 1 - Orangeville | 20:00 | Orangeville Athletic O45A | | Barrie FC O45A |
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| Fri | Jul 20 | Mens | West Orillia Sports Complex Turf | 21:00 | Orillia Inter Prem | | Alliston Arsenal (Prem) |
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| Sat | Jul 21 | U12GC | Fisher Field #6 | 12:00 | Collingwood United U12 Girls-Red | | North Bay Galaxy U11G |
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| Sat | Jul 21 | U12GC | Fisher Field #6 | 15:00 | Collingwood United U12G -White | | North Bay Galaxy U11G |
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| Sat | Jul 21 | U13BC | Henderson Park East | 14:00 | Bradford Eagles 2005B | | North Bay Selects U13B |
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| Sat | Jul 21 | U12GC | McCulley North Mini 2 | 13:00 | Huntsville Strikers U11G | | Barrie FC U12G2 |
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| Sat | Jul 21 | U13GC | Steve Omischl C1 | 15:00 | U13G North Bay Selects | | SSU 2005G |
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| Sun | Jul 22 | Mens | Galloway Park 1 | 17:00 | Huronia Saints (Div 1) | | Owen Sound Strikers |
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| Sun | Jul 22 | O35 | Gostick Park #1 | 16:00 | Muskoka United O35 | | Orillia DSC O35 |
