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| Mon | Sep 15 | MJC | Dufferin District 2 | 21:00 | IFC Men | 2 - 3 | No Finish Football Club |
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| Tue | Sep 16 | MRCE | Eastgate #1 | 21:00 | Peterborough City Men RCE | 3 - 4 | Olympiakos SC |
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| Tue | Sep 16 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Men Elite | 2 - 0 | Peniche CC |
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| Tue | Sep 16 | MOpCup | Sherwood Forest Park F5 | 21:00 | Burlington Bayhawks Men | 1 - 2 | Panathinaikos Elite |
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| Tue | Sep 16 | MRS | St. Marys High School | 21:00 | Hamilton Serbians | 0 - 2 | Sporting Club Ideal De Brampton |
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| Wed | Sep 17 | MPW | Corpus Christi | 21:00 | Croatia Norval | | Ebony Jrs |
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| Wed | Sep 17 | MRC | Earlscourt North | 21:00 | Toronto Irish FC | | Bolton Wanderers Men |
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| Wed | Sep 17 | MRCE | McNicoll Park | 21:00 | SPG Red Devils United | | Queens Park Rangers RCE |
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| Thu | Sep 18 | MRS | Clarkson Park | 21:00 | Clarkson SC | | Olimpia Toronto II |
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| Thu | Sep 18 | MRS | Eastview Full 3 | 21:00 | Guelph Royals RS | | Atletico Sporting Toronto Men |
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| Thu | Sep 18 | MJW | Meadowvale Park | 21:00 | North Mississauga Men | | Cambridge United Men |
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| Thu | Sep 18 | MElite | Southward 1 | 21:00 | Hrvat St. Catharines | | Olimpia Toronto Elite |
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| Thu | Sep 18 | MElite | Vaughan Grove Turf | 21:15 | Woodbridge Strikers Men Elite | | Panathinaikos Elite |
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| Fri | Sep 19 | MRS | Avondale Stadium | 21:00 | Sporting Club Ideal De Brampton | | Hamilton Serbians |
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| Fri | Sep 19 | MJW | Chris Gibson Park 1 | 21:00 | GTA United | | Woodbridge Strikers Men MJ |
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| Fri | Sep 19 | MPW | Dr. Martin Dobkin Park | 21:00 | Mississauga Croatia Men | | Caledon United FC Men |
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| Fri | Sep 19 | MPE | Eastview Park B | 21:00 | Barrie Blazers Men | | Queens Park Rangers PE |
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| Fri | Sep 19 | MPE | Fleming PYSC East Turf | 21:00 | Cavan FC Men | | Scarborough Rangers |
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| Fri | Sep 19 | MRC | Henderson Park East | 21:00 | Bradford Wolves Men | | SC Toronto Eagles Men |
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| Fri | Sep 19 | MPE | Highland Park | 21:00 | Aurora Hearts | | Toronto Celtic |
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| Fri | Sep 19 | MElite | Huron Park 2 Grass | 21:00 | Lakeshore United | | GS United Men Elite |
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| Fri | Sep 19 | MJC | Keelesdale | 21:00 | YJ Atletico FC Black | | Newmarket United Men |
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| Fri | Sep 19 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Guelph Royals Elite |
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| Fri | Sep 19 | MRCE | LAmoreaux #5 | 21:00 | Magic AC | | Artemisium FC |
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| Fri | Sep 19 | MJE | St. Robs CHS | 21:00 | Pana 2.0 | | CTSA Titans |
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| Sat | Sep 20 | MPW | Dr. Martin Dobkin Park | 20:00 | Distinctionz Men | | Croatia Norval |
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| Sat | Sep 20 | MJE | Harwood South 1 | 18:45 | Ajax Galacticos | | YJ Atletico FC Blue |
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| Sat | Sep 20 | MRCE | McNicoll Park | 19:00 | SPG Red Devils United | | Olympiakos SC |
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| Sun | Sep 21 | MRS | Brickyard | 16:00 | Olimpia Toronto II | | Atletico Sporting Toronto Men |
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| Sun | Sep 21 | MPE | Concord Thornhill Turf | 21:15 | Toronto Pamir | | RH PARS FC PE |
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| Sun | Sep 21 | MRCE | Dieppe Park | 16:00 | East York Men | | Queens Park Rangers RCE |
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| Sun | Sep 21 | MJC | Father Bulfon East | 19:00 | No Finish Football Club | | Barrie Spirit Men |
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| Sun | Sep 21 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | AIFC Men |
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| Sun | Sep 21 | MJW | Meadowvale Park | 16:30 | Prostars FC MJ | | International SC |
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| Sun | Sep 21 | MRS | Meadowvale Park | 18:30 | Prostars FC RS | | Globe FC |
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| Sun | Sep 21 | MRC | Sonoma Turf | 21:00 | KNSC Lions Men | | USC Karpaty Men |
