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| Mon | Aug 24 | WProv | Caledon R3 | 21:00 | Caledon United FC W Prov | 5 - 1 | GS United W Prov |
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| Mon | Aug 24 | MPE | Esther Shiner Stadium | 21:00 | North York Hearts | 0 - 2 | Toronto Irish FC |
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| Mon | Aug 24 | WRCE | LAmoreaux #5 | 21:00 | GS United W Reg | 3 - 2 | Cavan FC Women |
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| Tue | Aug 25 | MJE | Dr GW Williams SS | 19:00 | DFC Union Men | 1 - 3 | Stouffville Mustangs Blue |
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| Tue | Aug 25 | MElite | Earlscourt North | 21:10 | Peniche CC | | Toronto Celtic |
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| Tue | Aug 25 | M21RCE | LAmoreaux #5 | 19:00 | The SA U21M | 3 - 1 | Cavan FC U21M |
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| Wed | Aug 26 | WRCE | LAmoreaux #1 | 21:10 | GS United W Reg | | West Rouge Storm Black |
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| Wed | Aug 26 | MJE | LAmoreaux #5 | 21:10 | Scarborough Town FC MJ | | Scarboro Azzurri Blues MJ |
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| Wed | Aug 26 | MPW | Maple Park | 21:00 | Burlington Bayhawks | | Ebony Jrs |
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| Wed | Aug 26 | WRSW | Marden Park 1 | 21:00 | Rockwood FC Blue | | Banat FC |
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| Wed | Aug 26 | M21PS | St. Kateri Tekakwitha Turf | 21:00 | Croatia Norval U21M | | Whitecaps London U21M |
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| Wed | Aug 26 | MOpCup | Zanchin Automotive Soccer Centre Stadium | 21:00 | Toronto Pamir | | GS United Men |
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| Thu | Aug 27 | MRC | Barrie SC Development Centre | 21:00 | Barrie Blazers Men RC | | No Finish FC |
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| Thu | Aug 27 | MRS | Clarkson Park | 21:00 | Clarkson SC | | Globe FC |
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| Thu | Aug 27 | MPE | David Hamilton | 21:00 | RH PARS FC | | Toronto Pamir |
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| Thu | Aug 27 | MRCE | LAmoreaux #1 | 21:00 | Pana 2.0 | | Artemisium FC |
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| Thu | Aug 27 | M21RCE | Major Abbas Ali Park West | 21:00 | Olympic Flame K19 | | GS United U21M |
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| Thu | Aug 27 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Elite | | Olimpia Elite |
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| Thu | Aug 27 | WProv | RBJ Schlegel Park #2 (Huron) | 21:00 | Kitchener TFC Red | | King City Royals Women |
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| Thu | Aug 27 | MRC | Rob Ford Stadium | 21:00 | USC Karpaty Men RC | | Bradford Wolves |
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| Thu | Aug 27 | WRC | Sonoma Turf | 21:15 | KNSC Lions Women | | CFC Atletico Women |
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| Thu | Aug 27 | MElite | Southward 1 - 11v11 | 20:45 | Hrvat St. Catharines | | Croatia Norval Men |
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| Thu | Aug 27 | MJW | Trafalgar Sports Park 9 | 21:00 | Georgetown Mustangs Men | | Toronto Irish FC II |
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| Fri | Aug 28 | MJE | Bethesda #1 | 21:00 | Stouffville Mustangs Blue | | CFC Atletico Blue |
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| Fri | Aug 28 | MPW | Dr. Martin Dobkin Park | 21:00 | Mississauga Croatia Men | | Sporting Club Ideal De Brampton |
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| Fri | Aug 28 | MPE | Fleming Knights West Turf | 21:00 | Cavan FC Men | | QPR PE |
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| Fri | Aug 28 | MPW | Huron Park 2 Grass | 21:00 | Lakeshore United | | Burlington Bayhawks |
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| Fri | Aug 28 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Guelph Royals Elite |
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| Fri | Aug 28 | MRC | LAmoreaux #5 | 21:00 | Magic AC | | SC Toronto Eagles Men |
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| Fri | Aug 28 | MJW | York University Grass | 21:00 | FC E Etobicoke United FC | | Atletico Toronto |
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| Sat | Aug 29 | MJE | Ajax Turf Field | 18:45 | PFC Galacticos | | Ajax SC |
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| Sat | Aug 29 | MJE | Dunmoore Park | 17:00 | FCD Aces | | Stouffville Mustangs Yellow |
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| Sat | Aug 29 | MPE | McNicoll Park | 19:00 | SPG Red Devils United | | Woodbridge Strikers Men |
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| Sun | Aug 30 | MRCE | Beverley Morgan Park | 19:00 | QPR Reg | | Olympiakos SC |
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| Sun | Aug 30 | MRCE | Dieppe Park | 16:00 | East York Men | | Artemisium FC |
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| Sun | Aug 30 | MJW | Greenlane Sports Complex 2 | 20:00 | Paris FC | | Bolton Wanderers Blue Men |
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| Sun | Aug 30 | MJW | Keelesdale | 21:00 | CFC Atletico White | | Distinctionz Men MJ |
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| Sun | Aug 30 | MRCE | LAmoreaux #5 | 19:00 | Scarborough Rangers | | Peterborough City Men |
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| Sun | Aug 30 | MJW | Meadowvale (Syntex) | 14:00 | PRP FC | | CFC Atletico Black |
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| Sun | Aug 30 | MRS | Meadowvale (Syntex) | 18:00 | Prostars FC | | Olimpia Toronto II |
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| Sun | Aug 30 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Ebony Jrs |
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| Sun | Aug 30 | MJE | Richmond Green West | 17:00 | Richmond Hill Raiders | | Barrie Blazers Men MJ |
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| Sun | Aug 30 | M21RC | St. Joan of Arc | 18:00 | DFC Union Navy U21M | | KNSC Lions U21M |
