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| Mon | May 26 | W21RCE | Donegan Park | 20:00 | Northumberland United U21W | 1 - 4 | East York U21W |
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| Mon | May 26 | M21PS | Earlscourt North | 21:00 | SC Toronto Eagles U21M | 2 - 2 | USC Karpaty U21M |
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| Mon | May 26 | WProv | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Women | 2 - 2 | West Rouge Storm Prov |
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| Mon | May 26 | M21RCE | North Oshawa Park | 21:00 | Oshawa Turul U21M | 3 - 1 | NYFC Strikers U21M |
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| Mon | May 26 | W21RCE | Vaso Field | 20:00 | FC Durham U21W | 2 - 3 | Oshawa Kicks U21W |
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| Mon | May 26 | W21RS | Victoria Park Brampton | 21:00 | Brams United Red U21W | 0 - 1 | Burlington SC White U21W |
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| Mon | May 26 | WOpCup | Villanova Turf | 21:00 | King City Royals Women Prov | | Banat FC |
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| Tue | May 27 | WRS | Caledon R4 | 21:00 | Caledon United FC W RS | 0 - 3 | Toronto Azzurri Women |
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| Tue | May 27 | MPE | Centennial College Scarborough | 21:00 | Toronto Celtic | 1 - 1 | Aurora Hearts |
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| Tue | May 27 | MElite | Earlscourt North | 21:00 | Peniche CC | 0 - 3 | Hrvat St. Catharines |
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| Tue | May 27 | M21PC | Jayde Riviere Turf Field | 21:00 | Pickering FC U21M | 1 - 9 | NY Academy U21M PC |
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| Tue | May 27 | M21RC | McNaughton Turf | 21:00 | Vaughan Azzurri U21M RC | 1 - 2 | Glen Shields Juventus U21M |
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| Tue | May 27 | M21PC | North Maple Regional Park Turf # 2 | 21:00 | Vaughan Azzurri U21M PC | 1 - 2 | Union FC U21M |
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| Tue | May 27 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Men Elite | 4 - 1 | Scarboro Azzurri Blues Elite |
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| Tue | May 27 | WRCE | North Oshawa Park | 21:00 | Oshawa Kicks White | 3 - 1 | Peterborough City Women RCE |
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| Tue | May 27 | W21RC | Richmond Green East | 21:00 | Richmond Hill Raiders U21W | 2 - 0 | Barrie Spirit U21W |
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| Tue | May 27 | W21RSW | Waterdown District HS | 21:00 | Flamborough Dundas U21W | 3 - 0 | HEADS United Hurricanes U21W |
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| Wed | May 28 | WRCE | Centennial College Scarborough | 21:00 | West Rouge Storm White | 0 - 3 | West Rouge Storm Black |
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| Wed | May 28 | W21RCE | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks U21W | 1 - 1 | FC Emery Blizzards U21W |
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| Wed | May 28 | M21PS | Courtney Park | 21:00 | FC Toronto U21M | 1 - 1 | USC Karpaty U21M |
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| Wed | May 28 | WRC | Dr. Denison Turf - Newmarket | 21:15 | Newmarket United Women | 1 - 0 | Nottawasaga FC |
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| Wed | May 28 | M21RC | Eglinton Flats 11 | 19:00 | West Toronto United U21M | | Bradford Wolves U21M |
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| Wed | May 28 | M21RS | Iceland 2 | 21:00 | Dixie SC U21M | 2 - 0 | Mississauga Croatia U21M |
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| Wed | May 28 | M21RCE | LAmoreaux #5 | 21:10 | Scarborough Town FC U21M | 5 - 3 | Olympic Flame K19 |
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| Wed | May 28 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 19:00 | East York Men | 2 - 1 | Ebony Jrs |
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| Wed | May 28 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 21:00 | AC Diavoli | 3 - 1 | Magic AC |
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| Wed | May 28 | WRC | Villanova Turf | 21:00 | King City Royals Women RC | 0 - 0 | KNSC Lions Women |
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| Wed | May 28 | W21RSW | West Niagara SS | 20:30 | West Lincoln Dark Horse U21W | 1 - 2 | Burlington SC Blue U21W |
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| Thu | May 29 | WProv | Caledon R4 | 21:00 | Caledon United FC W Prov | 4 - 0 | Vaughan Azzurri Women |
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| Thu | May 29 | WProv | Centennial College Scarborough | 21:00 | West Rouge Storm Prov | | Gryphons FC Women |
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| Thu | May 29 | W21RC | Downsview Turf 2 | 21:15 | NT Nitros U21W | 2 - 2 | NYFC Strikers U21W |
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| Thu | May 29 | MOpCup | LAmoreaux #5 | 21:00 | Scarboro Azzurri Blues MJE | | Queens Park Rangers PE |
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| Thu | May 29 | M21RS | Mohawk 2 | 21:00 | Chantilly U21M | | Toronto United FC U21M |
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| Thu | May 29 | MOpCup | Ray Twinney #1 | 21:00 | Newmarket United Men | 0 - 1 | Clarkson SC |
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| Thu | May 29 | WRSW | RBJ Schlegel Park #1 (Villages) | 21:00 | Kitchener TFC Red Women | 2 - 0 | SSC Women |
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| Thu | May 29 | WProv | Villanova Turf | 21:00 | King City Royals Women Prov | 3 - 0 | Union FC Women |
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| Fri | May 30 | M21RCE | Centennial College Scarborough | 21:00 | The Scarborough Academy U21M | | King City Royals U21M |
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| Fri | May 30 | W21RC | Concord Thornhill Turf | 21:00 | Glen Shields Juventus U21W | | Markham Lightning U21W |
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| Fri | May 30 | MPW | Dr. Martin Dobkin Park | 21:00 | Mississauga Croatia Men | | Ebony Jrs |
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| Fri | May 30 | W21RS | Gryphon Soccer Complex 2 | 21:00 | Gryphons FC U21W | | Orangeville Storm FC U21W |
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| Fri | May 30 | MPE | Highland Park | 21:00 | Aurora Hearts | | Barrie Blazers Men |
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| Fri | May 30 | MJC | Keelesdale | 21:00 | YJ Atletico FC Black | | Barrie Spirit Men |
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| Fri | May 30 | MRCE | LAmoreaux #1 | 21:00 | Olympiakos SC | | Scarborough Town FC Men |
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| Fri | May 30 | WRS | Vaughan Grove 1 | 19:30 | Woodbridge Strikers Women | | Mississauga Croatia Women |
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| Fri | May 30 | MElite | Vaughan Grove 1 | 21:15 | Woodbridge Strikers Men Elite | | GS United Men Elite |
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| Sat | May 31 | MPW | Dr. Martin Dobkin Park | 20:00 | Distinctionz Men | | Fort Erie Sting |
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| Sat | May 31 | MJE | Harwood South 1 | 18:45 | Ajax Galacticos | | Pana 2.0 |
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| Sat | May 31 | MRC | Henderson Field | 19:00 | Union FC Men | | KNSC Lions Men |
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| Sat | May 31 | M21PC | Lamport Stadium | 14:00 | NY Academy U21M PC | | Vaughan Azzurri U21M PC |
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| Sat | May 31 | M21RC | Lamport Stadium | 18:00 | NY Academy U21M RC | | West Toronto United U21M |
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| Sat | May 31 | M21PC | University of Toronto Valley | 16:00 | Olympiacos Toronto K21 | | Pickering FC U21M |
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| Sun | Jun 1 | WRSW | Banat Park | 14:30 | Banat FC | | Rockwood FC Women |
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| Sun | Jun 1 | W21RC | Barrie SC Development Centre | 18:00 | Barrie Spirit U21W | | SC Toronto Eagles U21W |
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| Sun | Jun 1 | MRCE | Beverley Morgan Park | 19:00 | Queens Park Rangers RCE | | Peterborough City Men RCE |
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| Sun | Jun 1 | MRS | Brickyard | 16:00 | Olimpia Toronto II | | Globe FC |
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| Sun | Jun 1 | WRS | Brickyard | 18:00 | Olimpia Toronto Women | | Georgetown Mustangs Women |
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| Sun | Jun 1 | M21PS | Brickyard | 20:00 | Distinctionz U21M | | KNSC Lions U21M |
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| Sun | Jun 1 | WRSW | Budd Park 1 | 19:00 | Kitchener TFC Grey Women | | Kitchener TFC Red Women |
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| Sun | Jun 1 | M21RC | Centennial College Scarborough | 15:00 | CFC Black U21M | | Glen Shields Juventus U21M |
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| Sun | Jun 1 | MRCE | Dieppe Park | 16:00 | East York Men | | GS Vets |
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| Sun | Jun 1 | WRCE | Eastgate #1 | 19:00 | Peterborough City Women RCE | | Cavan FC Women |
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| Sun | Jun 1 | M21RC | Henderson Park East | 18:00 | Bradford Wolves U21M | | Barrie Spirit U21M |
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| Sun | Jun 1 | WOpCup | LAmoreaux #1 | 19:00 | GS United Women | | KNSC Lions Women |
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| Sun | Jun 1 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Panathinaikos Elite |
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| Sun | Jun 1 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Caledon United FC Men |
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| Sun | Jun 1 | MJW | Meadowvale Park | 16:30 | Prostars FC MJ | | Georgetown Mustangs Men |
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| Sun | Jun 1 | MJC | Rainbow Creek | 17:00 | No Finish Football Club | | Aurora Lions |
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| Sun | Jun 1 | W21RSW | RIM Park AF1 | 16:00 | BVB IA Waterloo U21W | | Burlington SC Blue U21W |
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| Sun | Jun 1 | WProv | Thames Centre ORC #2 | 20:00 | Alliance FC | | Gryphons FC Women |
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| Sun | Jun 1 | M21PS | The Hill Academy | 12:00 | AIFC U21M | | FC Toronto U21M |
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| Sun | Jun 1 | MPW | The Hill Academy | 16:30 | AIFC Men | | Croatia Norval |
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| Sun | Jun 1 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 11:00 | CTSA Titans | | Bradford Wolves Men |
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| Sun | Jun 1 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 13:00 | Vaughan Azzurri Women | | Roma Wolves |
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| Sun | Jun 1 | MOpCup | The Zanchin Automotive Soccer Centre Stadium | 15:00 | Toronto Tigers AST | | Olympiakos SC |
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| Sun | Jun 1 | MRCE | University of Toronto Valley | 17:00 | Artemisium FC | | Magic AC |
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| Sun | Jun 1 | WOpCup | Vaughan Grove 1 | 21:00 | Woodbridge Strikers Women | | Cambridge United Women |
