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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 | 2 - 3 | CTSA Titans |
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| Thu | May 8 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 19:00 | GTA United | 3 - 1 | Black Tigers FC |
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| Thu | May 8 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 21:00 | Toronto Tigers AST | 4 - 1 | Aurora Lions |
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| Sat | May 10 | MOpCup | St. Joan of Arc | 18:00 | Peterborough City Men MJE | 1 - 0 | Georgetown Mustangs Men |
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| Sat | May 10 | MOpCup | St. Joan of Arc | 20:00 | Ajax Galacticos | 1 - 2 | Barrie Spirit Men |
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| Sun | May 11 | MOpCup | Fleming PYSC East Turf | 18:00 | Cavan FC Men | 2 - 1 | Toronto Irish FC |
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| Sun | May 11 | MOpCup | Richmond Green West | 21:00 | RH PARS FC MJ | 2 - 4 | Pana 2.0 |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 14:00 | Peniche CC | 4 - 2 | Peterborough City Men RCE |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 16:00 | Vaughan Azzurri Men Elite | 5 - 4 | Cambridge United Men |
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| Sun | May 11 | MOpCup | St. Joan of Arc | 20:00 | North Mississauga Men | 1 - 2 | Queens Park Rangers RCE |
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| Sun | May 11 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 16:00 | Alliance FC | 8 - 0 | Peterborough City Women RCE |
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| Sun | May 11 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 18:00 | Kitchener TFC Red Women | 1 - 0 | West Rouge Storm Black |
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| Sun | May 11 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 20:00 | Globe FC | 2 - 4 | Scarborough Rangers |
