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| Mon | Jun 30 | U10B | Kitchener Park (Orillia) Field C | 19:00 | ODSC U10B Black | | CUSC U10B |
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| Wed | Jul 2 | U13B | Ferndale Park - Barrie | 19:00 | Barrie Cardinals U13B | 3 - 4 | WBSC U13B |
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| Wed | Jul 2 | U9B | Fisher Field #6 | 19:00 | CUSC U9B | | Barrie SC U9B |
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| Wed | Jul 2 | U14GCC | G.S. Gaston Sports Park 5 | 19:00 | SSU U14G | 0 - 3 | CUSC U14G |
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| Wed | Jul 2 | U9B | G.S. Gaston Sports Park C | 19:00 | SSU U9B | 15 - 0 | MUFC U9B |
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| Wed | Jul 2 | U11G | Galloway Park 1 | 19:00 | North Simcoe Rangers U11G | 0 - 11 | MUFC U11G |
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| Wed | Jul 2 | U12G | Gostick Park #1B | 19:00 | MUFC U12G | 0 - 2 | CUSC U12G |
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| Wed | Jul 2 | O45 | Gostick Park #2 | 21:00 | Muskoka O45 | 4 - 4 | Nottawasaga FC O45 |
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| Wed | Jul 2 | U9B | Henderson Park 3A | 18:30 | BWFC U9B | 2 - 2 | ODSC U9B |
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| Wed | Jul 2 | O35 | Henderson Park East | 21:00 | Bradford Wolves FC O35 | 3 - 0 | Union Vintage O35 |
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| Wed | Jul 2 | U9B | Livingstone Park A | 19:00 | Barrie Cardinals U9B | 5 - 1 | Innisfil SC U9B |
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| Wed | Jul 2 | U12G | Mel Mitchell C | 19:00 | SSU U12G | 2 - 3 | Barrie Spirit U12G White |
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| Wed | Jul 2 | U9B | Nipissing University | 19:00 | NDSC U8B | 0 - 5 | NDSC U9B |
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| Wed | Jul 2 | U13B | West Orillia Sports Complex Grass | 19:00 | ODSC U13B | 5 - 3 | Barrie Spirit U13B Gold |
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| Thu | Jul 3 | U11B | Assikinack Public School | 19:00 | Barrie Cardinals U11B | | ODSC U11B |
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| Thu | Jul 3 | U11B | Barrie SC Trg Field | 18:30 | Barrie SC U11B | 3 - 3 | WBSC U11B |
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| Thu | Jul 3 | U16BCC | Fisher Field #1 | 21:00 | CUSC U16B | 3 - 1 | Bradford Wolves U15B |
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| Thu | Jul 3 | O45 | Innisfil Recreation Complex 3 | 20:30 | Barrie Masters O45 | 4 - 3 | Orillia Inter O45 |
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| Thu | Jul 3 | U10G | Marsellus Park | 18:30 | Barrie SC U10G | 3 - 1 | ODSC U10G |
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| Thu | Jul 3 | U11B | Mel Mitchell C | 19:00 | SSU U11B | | Innisfil SC U11B |
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| Thu | Jul 3 | U11B | Pollington Field 5 (U11/12 Rep) | 19:15 | MUFC U11B | 3 - 6 | CUSC U11B |
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| Fri | Jul 4 | U10B | Fisher Field #8 | 19:00 | CUSC U10B | | MUFC U10B |
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| Fri | Jul 4 | O35 | Henderson Field | 21:00 | Americas United O35 | | Innisfil Greyhounds O35 |
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| Fri | Jul 4 | O35 | Henderson Park West | 21:00 | 1857 FC O35 | | Barrie SOP O35 |
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| Fri | Jul 4 | Mens | West Orillia Sports Complex Turf | 21:00 | Orillia Inter | | NSSC Rangers |
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| Sat | Jul 5 | U14B | Eastview Park B | 11:00 | Barrie SC U14B | | NDSC U14B |
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| Sat | Jul 5 | U14GC | Steve Omischl Coca Cola | 13:00 | NDSC U14G | | CUSC U14G |
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| Sat | Jul 5 | U14B | West Orillia Sports Complex Grass | 15:00 | ODSC U14B | | NDSC U14B |
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| Sun | Jul 6 | U9G | Fisher Field #6 | 12:00 | NDSC U9G | | CUSC U9G |
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| Sun | Jul 6 | U9G | Fisher Field #6 | 14:00 | CUSC U9G | | NDSC U9G |
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| Sun | Jul 6 | U10G | Mel Mitchell A | 10:00 | SSU U10G | | GSSC U10G |
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| Sun | Jul 6 | U10G | Mel Mitchell A | 12:00 | GSSC U10G | | SSU U10G |
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| Sun | Jul 6 | Mens | Nottawasaga Inn #1 | 18:00 | Alliston FC | | Alliston United |
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| Sun | Jul 6 | U11B | Pollington Field 5 (U11/12 Rep) | 16:00 | MUFC U11B | | GSSC U10B2 |
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| Sun | Jul 6 | U16B | Queens Athletic Field | 15:00 | GSSC U16B | | Bradford Wolves U15B |
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| Sun | Jul 6 | U12G | West Orillia Sports Complex Mini 1 | 11:00 | ODSC U12G | | NDSC U12G |
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| Sun | Jul 6 | U12G | West Orillia Sports Complex Mini 1 | 13:00 | NDSC U12G | | ODSC U12G |
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| Sun | Jul 6 | U11B | West Orillia Sports Complex Mini 2 | 11:00 | ODSC U11B | | GSSC U10B2 |
