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| Mon | May 5 | MOpCup | St. Joan of Arc | 19:00 | No Finish Football Club | 2 - 1 | IFC Men |
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| Mon | May 5 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 19:00 | Scarboro Azzurri Blues MJE | 4 - 2 | Prostars FC MJ |
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| Mon | May 5 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 21:00 | Newmarket United Men | 3 - 0 | Toronto Irish FC II |
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| Tue | May 6 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 19:00 | Woodbridge Strikers Men MJ | 1 - 3 | YJ Atletico FC Blue |
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| Tue | May 6 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 21:00 | Markham Lightning | 2 - 0 | International SC |
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| Wed | May 7 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 20:00 | YJ Atletico FC Black | | CTSA Titans |
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| Thu | May 8 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 19:00 | GTA United | | Black Tigers FC |
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| Thu | May 8 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 21:00 | Toronto Tigers AST | | Aurora Lions |
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| Sat | May 10 | MOpCup | St. Joan of Arc | 18:00 | Peterborough City Men MJE | | Georgetown Mustangs Men |
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| Sat | May 10 | MOpCup | St. Joan of Arc | 20:00 | Ajax Galacticos | | Barrie Spirit Men |
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| Sun | May 11 | MOpCup | Fleming PYSC East Turf | 18:00 | Cavan FC Men | | Toronto Irish FC |
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| Sun | May 11 | MOpCup | Richmond Green West | 21:00 | RH PARS FC MJ | | Pana 2.0 |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 14:00 | Peniche CC | | Peterborough City Men RCE |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 16:00 | Vaughan Azzurri Men Elite | | Cambridge United Men |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 20:00 | North Mississauga Men | | Queens Park Rangers RCE |
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| Sun | May 11 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 16:00 | Alliance FC | | Peterborough City Women RCE |
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| Sun | May 11 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 18:00 | Kitchener TFC Red Women | | West Rouge Storm Black |
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| Sun | May 11 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 20:00 | Globe FC | | Scarborough Rangers |
