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| Mon | May 14 | CRE21 | Courtice South | 21:00 | Darlington Energy | 4 - 0 | North York Explosion |
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| Mon | May 14 | Prov E | McNaughton Turf | 21:00 | Vaughan Azzurri | 1 - 1 | Durham United |
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| Mon | May 14 | CRE | Mount Albert Lions #2 | 21:00 | East Gwillimbury Talons | 2 - 3 | North York Panthers |
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| Tue | May 15 | CR | Caledon R3 | 21:00 | Caledon Ladies FC | 0 - 0 | Nottawasaga FC |
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| Tue | May 15 | PE21 | LAmoreaux #1 | 21:00 | GS United | 0 - 0 | FC Durham Academy |
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| Tue | May 15 | Prov E | University of Guelph East | 21:00 | Guelph Gryphons | 1 - 1 | Woodbridge Strikers |
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| Wed | May 16 | P21S | Bishop Ryan HS | 21:00 | Hamilton United U21 | 2 - 0 | Oakville Blue Devils U21 |
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| Wed | May 16 | PC | Centennial College Scarborough | 21:00 | West Rouge Storm | 0 - 0 | King City Royals |
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| Wed | May 16 | SR21 | Citywide Soccer | 21:00 | FC London | 6 - 0 | Milton Magic GU21A |
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| Wed | May 16 | PE21 | Concord Thornhill Turf | 21:00 | Vaughan Azzurri | 4 - 2 | Saltfleet Stoney Creek |
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| Wed | May 16 | Prov E | Downsview Dome | 21:00 | North Toronto Nitros | 2 - 2 | Waterloo Wildfire |
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| Wed | May 16 | CR | Dr. Denison Turf - Newmarket | 21:00 | Newmarket United | 3 - 3 | Aurora Spurs |
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| Wed | May 16 | PE21 | Lancaster Park | 21:00 | St. Catharines Jets | 2 - 2 | North Mississauga Black |
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| Wed | May 16 | CRE | Milliken Mills Complex E | 21:00 | UMSC Strikers | 0 - 1 | Peterborough City |
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| Wed | May 16 | PE21 | Norton Park North | 21:00 | Burlington Bayhawks | 2 - 0 | Toronto Blizzard |
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| Wed | May 16 | CRE | Richmond Green East | 21:00 | Richmond Hill Raiders | 0 - 2 | West Rouge |
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| Wed | May 16 | SR21 | Sherwood Forest Park F5 | 21:00 | Burlington Bayhawks G99BL | 0 - 0 | Saltfleet Stoney Creek Orange |
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| Wed | May 16 | CRE | Whitby Soccer Centre Dome (11v11) | 21:00 | Whitby Iroquois | 4 - 0 | Oshawa Kicks |
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| Thu | May 17 | PC | Dufferin District 2 | 21:00 | Vaughan Azzurri | 3 - 0 | GS United |
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| Thu | May 17 | CR21 | Eidelweiss Park 5 | 21:00 | Bolton Wanderers | 3 - 0 | Huronia Saintes |
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| Thu | May 17 | P21S | Kalar Sports Park #6 Turf | 21:00 | Niagara United | 0 - 2 | FC London P21 |
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| Thu | May 17 | P21C | Milliken Mills Complex E | 21:00 | UMSC Strikers U21 | 0 - 7 | Markham Lightning |
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| Thu | May 17 | CRE21 | North Oshawa Park | 21:00 | Oshawa Kicks U21 | 0 - 3 | Peterborough City White |
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| Thu | May 17 | PS | Norton Park South | 21:00 | BWRSL Tigers | 3 - 6 | Hamilton Sparta |
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| Thu | May 17 | CR | Trafalgar Sports Park 10 | 21:00 | Georgetown Mustangs | 1 - 1 | Caledon Wildcats |
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| Thu | May 17 | PS | University of Guelph East | 21:00 | Guelph Gryphons | 1 - 0 | North Mississauga Black |
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| Thu | May 17 | P21S | University of Guelph West U13+ | 21:00 | Guelph Gryphons | 1 - 1 | Kitchener Spirit U21 |
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| Fri | May 18 | PC | LAmoreaux #5 | 21:00 | MFA Gunners | 0 - 5 | Richmond Hill Raiders |
