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| Mon | Jul 27 | M21RS | Andrew McCandless Park 1 | 21:00 | SSE 90 U21M | 1 - 2 | NT Nitros U21M |
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| Mon | Jul 27 | M21RCE | Consumers Field South | 21:00 | Whitby FC U21M | 1 - 3 | Cavan FC U21M |
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| Mon | Jul 27 | M21RCE | Darlington Field #3 | 21:00 | Darlington Energy U21M | 1 - 5 | Olympic Flame K19 |
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| Mon | Jul 27 | M21RC | Dufferin District 1 | 21:00 | IFC U21M | 4 - 2 | Barrie Spirit U21M |
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| Mon | Jul 27 | MRC | Earlscourt North | 21:00 | SC Toronto Eagles Men | 1 - 4 | Barrie Blazers Men RC |
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| Mon | Jul 27 | M21RCE | Firgrove Park | 19:00 | Asante Elite U21M | 4 - 0 | GS United U21M |
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| Mon | Jul 27 | WRCE | Fleming Knights West Turf | 21:00 | Cavan FC Women | 0 - 2 | PFC Valkyries |
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| Mon | Jul 27 | WOpCup | LAmoreaux #1 | 21:10 | GS United W Prov | | Toronto Azzurri |
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| Mon | Jul 27 | M21RSW | Laurier University Stadium | 21:00 | Waterloo United U21M | 3 - 2 | Gryphons FC U21M |
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| Mon | Jul 27 | W21RCE | North Oshawa Park | 21:00 | Oshawa Kicks U21W | 0 - 4 | GFA Yellow |
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| Mon | Jul 27 | W21RS | Norton Community Park F2 | 21:00 | Burlington SC Blue U21W | 1 - 2 | Waterloo United U21W |
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| Mon | Jul 27 | MPW | Orchard Community Park (F1) | 21:00 | Burlington Bayhawks | 3 - 1 | Mississauga Croatia Men |
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| Mon | Jul 27 | WRC | St. Joan of Arc | 21:00 | DFC Union Women | 0 - 1 | Nottawasaga FC |
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| Tue | Jul 28 | WRS | Barbour Field 1 | 21:00 | HEADS United Hurricanes | 0 - 3 | Banat FC |
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| Tue | Jul 28 | WRC | Caledon R4 | 21:00 | Caledon United FC W Reg | 0 - 2 | NYC Panthers |
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| Tue | Jul 28 | WRSW | Cowan - Guarantee | 20:30 | Woodstock FC Women | 4 - 0 | Flamborough Dundas |
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| Tue | Jul 28 | W21RCE | Downsview Turf 3 | 19:00 | NYFC Strikers U21W | 2 - 0 | East York U21W |
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| Tue | Jul 28 | M21PC | Grovewood Park | 21:00 | Oak Ridges Knights U21M Prov | 2 - 1 | Thornhill Bolts U21M |
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| Tue | Jul 28 | WRSW | Marden Park 1 | 21:00 | Rockwood FC Blue | 8 - 1 | Cambridge United Women |
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| Tue | Jul 28 | W21RC | McNaughton Turf | 21:00 | Vaughan Azzurri U21W | 0 - 4 | Etobicoke FC U21W |
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| Tue | Jul 28 | MRS | Nora Frances Henderson Football Field | 21:00 | Globe FC | 3 - 5 | GTA United |
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| Tue | Jul 28 | WRCE | North Oshawa Park | 21:00 | Oshawa Kicks White | 5 - 2 | Peterborough City Women |
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| Tue | Jul 28 | W21RS | Notre Dame HS Burlington | 21:00 | Force Academy U21W | 0 - 0 | Alliance FC Mustangs U21W |
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| Tue | Jul 28 | M21PS | St. Francis Xavier Catholic SS Milton | 21:00 | Scrosoppi FC U21M | 0 - 8 | Croatia Norval U21M |
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| Tue | Jul 28 | M21RS | Trafalgar Sports Park 9 | 21:00 | Georgetown Mustangs U21M | 3 - 5 | DFC Union Orange U21M |
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| Tue | Jul 28 | MRS | University of Guelph East | 21:00 | Guelph Royals RS | 3 - 0 | Prostars FC |
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| Wed | Jul 29 | WRC | Cherry Beach West | 21:00 | SC Toronto Eagles Women | 2 - 0 | Mississauga Croatia Women |
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| Wed | Jul 29 | WRCE | Civic Field #3 (Durham) | 21:00 | Oshawa Kicks Red | 0 - 3 | Pickering FC Women |
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| Wed | Jul 29 | WRC | Clarkson SS Turf | 21:00 | Olimpia Toronto Women | 1 - 0 | Newmarket United II W |
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| Wed | Jul 29 | M21PC | Concord Thornhill Turf | 21:00 | GFC Juve U21M | 5 - 0 | NY Academy U21M |
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| Wed | Jul 29 | MPE | Earlscourt North | 21:00 | Toronto Irish FC | 1 - 1 | Cavan FC Men |
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| Wed | Jul 29 | M21PS | Edelweiss Soccer Park 5-R3 | 21:00 | Bolton Wanderers White U21M | 4 - 5 | Toronto United FC U21M |
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| Wed | Jul 29 | WRS | Gryphon Soccer Complex 1 | 21:00 | Gryphons FC Women | 0 - 2 | SSC Women |
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| Wed | Jul 29 | MJW | Humberview SS | 21:00 | Caledon United FC Men | 7 - 2 | Bolton Wanderers Blue Men |
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| Wed | Jul 29 | M21PS | Iceland 1 | 21:00 | Dixie U21M | 8 - 2 | USC Karpaty U21M |
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| Wed | Jul 29 | W21RS | Kiwanis Park - Niagara | 21:00 | Roma Wolves U21W | 2 - 6 | RED Academy U21W |
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| Wed | Jul 29 | MElite | LAmoreaux #1 | 21:10 | GS United Men | 4 - 1 | Scarboro Azzurri Blues Elite |
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| Wed | Jul 29 | MJE | LAmoreaux #5 | 21:10 | Scarborough Town FC MJ | 2 - 5 | Barrie Blazers Men MJ |
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| Wed | Jul 29 | WRSW | Marden Park 1 | 21:00 | Rockwood FC Blue | 0 - 0 | Rockwood FC Black |
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| Wed | Jul 29 | M21RC | Villanova Turf | 21:00 | King City Royals U21M | 6 - 0 | Barrie Spirit U21M |
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| Wed | Jul 29 | M21RSW | Waterloo Oxford SS Main | 21:00 | Eagles 1982 U21M | 2 - 2 | Woodstock FC U21M |
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| Thu | Jul 30 | WProv | Azzurri Stadium TO | 21:00 | Toronto Azzurri | 0 - 1 | Caledon United FC W Prov |
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| Thu | Jul 30 | M21RC | Berczy Park Centre | 19:00 | UMSC U21M | 3 - 1 | Vaughan Azzurri U21M |
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| Thu | Jul 30 | MElite | Centennial Bowl Guelph | 21:00 | Guelph Royals Elite | 2 - 2 | Toronto Celtic |
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| Thu | Jul 30 | MRS | Clarkson Park | 21:00 | Clarkson SC | 3 - 0 | Atletico Sporting Toronto Men |
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| Thu | Jul 30 | MPE | David Hamilton | 21:00 | RH PARS FC | 1 - 0 | Woodbridge Strikers Men |
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| Thu | Jul 30 | W21RC | Edelweiss Soccer Park 5-R2 | 21:00 | Bolton Wanderers U21W | 1 - 1 | DFC Union U21W |
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| Thu | Jul 30 | M21RSW | Heritage Green #2 | 21:00 | Hamilton Croatia U21M | 5 - 0 | Gryphons FC U21M |
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| Thu | Jul 30 | W21RCE | Jayde Riviere Turf Field | 21:00 | Pickering FC U21W | 3 - 0 | East York U21W |
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| Thu | Jul 30 | MJW | Kiwanis - Georgetown | 21:00 | Georgetown Mustangs Men | 1 - 3 | FC E Etobicoke United FC |
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| Thu | Jul 30 | WProv | LAmoreaux #1 | 21:10 | GS United W Prov | 8 - 1 | Vaughan Azzurri Women |
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| Thu | Jul 30 | W21RS | Maple Park | 21:00 | Force Academy U21W | 4 - 1 | SSC U21W |
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| Thu | Jul 30 | W21RCE | Massey Grove Park | 21:00 | NYFC Strikers U21W | 6 - 1 | Whitby FC U21W |
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| Thu | Jul 30 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Elite | 2 - 0 | Panathinaikos |
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| Thu | Jul 30 | MPW | Orchard Park SS | 20:00 | Hamilton Serbians | 2 - 0 | AC Diavoli |
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| Thu | Jul 30 | WProv | RBJ Schlegel Park #2 (Huron) | 21:00 | Kitchener TFC Red | 2 - 1 | Alliance FC Mustangs Women |
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| Thu | Jul 30 | MOpCup | Save Max Sports Centre Field 1 | 20:30 | Lakeshore United | 0 - 2 | Olimpia Elite |
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| Thu | Jul 30 | MElite | Southward 1 - 11v11 | 20:45 | Hrvat St. Catharines | 3 - 2 | Peniche CC |
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| Thu | Jul 30 | MRC | Verstraten Park | 21:00 | Barrie Blazers Men RC | 7 - 1 | KNSC Lions Men |
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| Thu | Jul 30 | WProv | Villanova Turf | 21:00 | King City Royals Women | 0 - 1 | Newmarket United W Prov |
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| Fri | Jul 31 | MJW | Keelesdale | 21:00 | CFC Atletico Black | | CFC Atletico White |
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| Fri | Jul 31 | M21PC | LAmoreaux #1 | 21:00 | Olympiacos Toronto K21 | 0 - 2 | Power FC U21M |
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| Fri | Jul 31 | M21RC | Sir William Mulock - Newmarket | 21:00 | DFC Union Navy U21M | 12 - 0 | IFC U21M |
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| Sun | Aug 2 | MJE | Dunmoore Park | 18:30 | FCD Aces | | PFC Galacticos |
