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| Mon | Sep 14 | M21PC | Berczy Park North | 21:00 | Jarvis SC U21M | 2 - 0 | Olympiacos Toronto K21 |
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| Mon | Sep 14 | MRC | Earlscourt North | 21:00 | SC Toronto Eagles Men | 0 - 4 | Bradford Wolves |
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| Mon | Sep 14 | MRCE | LAmoreaux #1 | 21:00 | Scarborough Rangers | 4 - 4 | Pana 2.0 |
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| Mon | Sep 14 | MPW | Orchard Community Park (F1) | 21:00 | Burlington Bayhawks | | AC Diavoli |
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| Tue | Sep 15 | MElite | Earlscourt North | 21:10 | Peniche CC | 2 - 0 | Guelph Royals Elite |
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| Tue | Sep 15 | MPE | LAmoreaux #1 | 21:00 | QPR PE | 1 - 3 | Woodbridge Strikers Men |
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| Wed | Sep 16 | MJE | Bethesda #1 | 20:00 | Stouffville Mustangs Yellow | | Stouffville Mustangs Blue |
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| Wed | Sep 16 | WRC | Cherry Beach West | 21:00 | SC Toronto Eagles Women | | CFC Atletico Women |
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| Wed | Sep 16 | MPE | Earlscourt North | 21:00 | Toronto Irish FC | | RH PARS FC |
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| Wed | Sep 16 | MOpCup | LAmoreaux #1 | 21:15 | GS United Men | | Hamilton Serbians |
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| Wed | Sep 16 | MRCE | LAmoreaux #5 | 21:10 | Scarborough Town FC RCE | | East York Men |
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| Thu | Sep 17 | MElite | Centennial Bowl Guelph | 21:00 | Guelph Royals Elite | | Panathinaikos |
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| Thu | Sep 17 | MRS | Clarkson Park | 21:00 | Clarkson SC | | Bolton Wanderers White Men RS |
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| Thu | Sep 17 | MPW | Jean Augustine Stadium | 21:00 | Sporting Club Ideal De Brampton | | Ebony Jrs |
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| Thu | Sep 17 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Elite | | Hrvat St. Catharines |
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| Fri | Sep 18 | MPW | Dr. Martin Dobkin Park | 21:00 | Mississauga Croatia Men | | Lakeshore United |
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| Fri | Sep 18 | MJW | Edelweiss Soccer Park 5-R3 | 21:00 | Bolton Wanderers Blue Men | | FC E Etobicoke United FC |
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| Fri | Sep 18 | MRC | Henderson Park East | 21:00 | Bradford Wolves | | Magic AC |
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| Fri | Sep 18 | MJW | Keelesdale | 21:00 | CFC Atletico Black | | Caledon United FC Men |
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| Fri | Sep 18 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Croatia Norval Men |
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| Fri | Sep 18 | MElite | Paramount Fine Foods Centre 1 | 21:00 | Olimpia Elite | | GS United Men |
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| Fri | Sep 18 | MRC | Sonoma Turf | 21:00 | KNSC Lions Men | | USC Karpaty Men RC |
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| Fri | Sep 18 | MPE | Vaughan Grove 1 | 21:15 | Woodbridge Strikers Men | | Toronto Irish FC |
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| Fri | Sep 18 | MRS | Victoria Park Brampton | 21:00 | GTA United | | Olimpia Toronto II |
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| Sat | Sep 19 | MJW | Brickyard | 16:00 | Toronto Tigers AST | | Paris FC |
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| Sat | Sep 19 | MJW | Centennial Park East Sports Hub - Field 1 | 18:15 | USC Karpaty Men MJW | | Distinctionz Men MJ |
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| Sat | Sep 19 | MPE | McNicoll Park | 19:00 | SPG Red Devils United | | Cavan FC Men |
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| Sun | Sep 20 | MJE | Bethesda #1 | 20:00 | Stouffville Mustangs Yellow | | Barrie Blazers Men MJ |
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| Sun | Sep 20 | MRS | Brickyard | 16:00 | Olimpia Toronto II | | Globe FC |
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| Sun | Sep 20 | MElite | Christ The King CSS | 18:00 | Croatia Norval Men | | Vaughan Azzurri Elite |
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| Sun | Sep 20 | MPE | Concord Thornhill Turf | 20:00 | Toronto Pamir | | North York Hearts |
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| Sun | Sep 20 | MRCE | Eastgate #1 | 16:00 | Peterborough City Men | | Pana 2.0 |
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| Sun | Sep 20 | MJW | Keelesdale South Park | 21:00 | CFC Atletico White | | Georgetown Mustangs Men |
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| Sun | Sep 20 | MElite | LAmoreaux #1 | 19:00 | Panathinaikos | | Toronto Celtic |
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| Sun | Sep 20 | MRCE | LAmoreaux #1 | 21:00 | Artemisium FC | | Scarborough Town FC RCE |
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| Sun | Sep 20 | MRCE | LAmoreaux #5 | 19:00 | Scarborough Rangers | | QPR Reg |
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| Sun | Sep 20 | MJW | Meadowvale (Syntex) | 14:00 | Toronto Tigers AST | | PRP FC |
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| Sun | Sep 20 | MRS | Meadowvale (Syntex) | 18:00 | Prostars FC | | Guelph Royals RS |
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| Sun | Sep 20 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Distinctionz Men PW |
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| Sun | Sep 20 | MRC | Sonoma Turf | 15:00 | KNSC Lions Men | | No Finish FC |
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| Sun | Sep 20 | MPW | Victoria Park Brampton | 14:30 | Ebony Jrs | | Hamilton Serbians |
