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| Mon | Aug 8 | CR | Earlscourt North | 21:00 | SC Toronto | | Aurora Spurs |
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| Tue | Aug 9 | SR | Bishop Ryan HS | 21:00 | West Lincoln Sharks | | Mississauga Croatia |
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| Tue | Aug 9 | CR | Caledon R4 | 21:00 | Caledon United FC | | Nottawasaga FC |
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| Tue | Aug 9 | Prov | Gryphon Soccer Complex 2 | 21:00 | Guelph Gryphons FC Black | | Ajax SC |
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| Tue | Aug 9 | CRE21 | Kinsmen Turf | 21:00 | Pickering FC | | Woodbridge Strikers Blue |
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| Tue | Aug 9 | SR21 | RIM Park AF2 | 21:00 | BVB IA Waterloo | | Club Roma Soccer |
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| Tue | Aug 9 | SR21 | West Lincoln Leisureplex 2 | 21:00 | West Lincoln Warriors | | Roma Wolves NRSP |
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| Wed | Aug 10 | CRE | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks Red | | Peterborough City |
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| Wed | Aug 10 | CRE | Fleming Knights West Turf | 21:00 | Northumberland United | | Oshawa Kicks White |
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| Wed | Aug 10 | SR | Loyola SS | 21:00 | Mississauga Croatia | | Georgetown SC |
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| Wed | Aug 10 | CR | McNicoll Park | 21:00 | Etobicoke FC | | King City Royals |
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| Wed | Aug 10 | SR | Milton Community Park #1 | 21:00 | Milton Magic | | Brampton Elite Soccer Academy |
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| Wed | Aug 10 | Prov | Sheppards Bush Turf | 21:00 | Aurora WFC | | GS United |
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| Wed | Aug 10 | SR21 | Sir Winston Turf Field | 21:00 | Roma Wolves NRSP | | Burlington Bayhawks |
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| Thu | Aug 11 | Prov | Caledon R3 | 21:00 | Caledon United FC | | King City Royals |
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| Thu | Aug 11 | CRE | Cherry Beach West | 21:00 | North York Cosmos Panthers | | Toronto Skillz |
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| Thu | Aug 11 | CR21 | Eidelweiss Soccer Field 4-R2 | 21:00 | Bolton U21 White | | Woodbridge Strikers Red |
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| Thu | Aug 11 | Prov | University of Guelph Varsity | 21:00 | Guelph Gryphons FC Red | | West Rouge Storm |
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| Thu | Aug 11 | CRE21 | Vaughan Grove 1 | 21:00 | Woodbridge Strikers Blue | | East York |
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| Sat | Aug 13 | Prov21 | The Hill Academy | 16:30 | Athlete Institute FC | | FC Durham Academy |
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| Sun | Aug 14 | Prov | Banat Park | 16:00 | Banat FC | | Caledon United FC |
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| Sun | Aug 14 | CRE | Eastgate #2 | 16:00 | Peterborough City | | North York Cosmos Panthers |
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| Sun | Aug 14 | SR | Nilestown Polish Canadian SC | 16:00 | Alliance FC Galaxy | | Brams United |
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| Sun | Aug 14 | CR | Nottawasaga Inn #1 | 14:00 | Nottawasaga FC | | Newmarket United |
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| Sun | Aug 14 | SR | Victoria Park Brampton | 19:00 | Brampton Elite Soccer Academy | | West Lincoln Sharks |
