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| Tue | Sep 2 | MElite | Clarkson SS Turf | 21:00 | Olimpia Toronto Elite | 5 - 3 | Panathinaikos Elite |
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| Tue | Sep 2 | MRCE | Eastgate #1 | 21:00 | Peterborough City Men RCE | 2 - 2 | Artemisium FC |
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| Tue | Sep 2 | MPE | LAmoreaux #1 | 21:00 | Queens Park Rangers PE | 2 - 3 | Scarborough Rangers |
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| Tue | Sep 2 | WRS | McNicoll Park | 19:00 | NYC Panthers Women | 3 - 1 | Caledon United FC W RS |
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| Tue | Sep 2 | MOpCup | St. John Henry Newman Catholic SS | 21:00 | Hamilton Serbians | 2 - 3 | Burlington Bayhawks Men |
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| Wed | Sep 3 | MJE | Cornell CC | 21:00 | Markham Lightning | | YJ Atletico FC Blue |
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| Wed | Sep 3 | MJC | Earlscourt North | 21:00 | Toronto Irish FC II | | Newmarket United Men |
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| Wed | Sep 3 | WOpCup | The Zanchin Automotive Soccer Centre Stadium | 20:00 | Caledon United FC W Prov | | GS United Women |
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| Wed | Sep 3 | MJW | Trafalgar Sports Park 9 | 21:00 | Georgetown Mustangs Men | | North Mississauga Men |
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| Thu | Sep 4 | MElite | Centennial Bowl Guelph | 21:00 | Guelph Royals Elite | | Vaughan Azzurri Men Elite |
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| Thu | Sep 4 | MRC | Earlscourt North | 21:00 | SC Toronto Eagles Men | | Toronto Irish FC |
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| Thu | Sep 4 | MRC | Henderson Park East | 21:00 | USC Karpaty Men | | Bradford Wolves Men |
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| Thu | Sep 4 | MJE | LAmoreaux #5 | 21:00 | Scarboro Azzurri Blues MJE | | CTSA Titans |
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| Thu | Sep 4 | MRS | St. Jean de Brebeuf School | 21:00 | Hamilton Serbians | | Prostars FC RS |
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| Fri | Sep 5 | MPW | Caledon R3 | 21:00 | Caledon United FC Men | | Fort Erie Sting |
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| Fri | Sep 5 | MJW | Chris Gibson Park 1 | 21:00 | GTA United | | Toronto Tigers AST |
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| Fri | Sep 5 | MPW | Dr. Martin Dobkin Park | 21:00 | Mississauga Croatia Men | | Croatia Norval |
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| Fri | Sep 5 | MPE | Fleming PYSC East Turf | 21:00 | Cavan FC Men | | RH PARS FC PE |
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| Fri | Sep 5 | MJC | Highland Park | 21:00 | Aurora Lions | | Toronto Irish FC II |
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| Fri | Sep 5 | MElite | Huron Park 2 Grass | 21:00 | Lakeshore United | | Panathinaikos Elite |
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| Fri | Sep 5 | MElite | LAmoreaux #1 | 21:00 | Scarboro Azzurri Blues Elite | | Peniche CC |
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| Fri | Sep 5 | MJW | Vaughan Grove Turf | 21:15 | Woodbridge Strikers Men MJ | | International SC |
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| Sat | Sep 6 | MJC | Maple Ridge SS | 17:00 | Barrie Spirit Men | | IFC Men |
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| Sat | Sep 6 | MRCE | McNicoll Park | 19:00 | SPG Red Devils United | | Artemisium FC |
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| Sat | Sep 6 | MRS | St. Joan of Arc | 20:00 | Atletico Sporting Toronto Men | | Guelph Royals RS |
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| Sun | Sep 7 | MElite | Bishop Macdonell HS | 16:00 | Guelph Royals Elite | | Peniche CC |
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| Sun | Sep 7 | MPE | Concord Thornhill Turf | 20:30 | Toronto Pamir | | Queens Park Rangers PE |
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| Sun | Sep 7 | MRCE | Dieppe Park | 16:00 | East York Men | | Olympiakos SC |
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| Sun | Sep 7 | MRC | Edelweiss Soccer Park 5-R3 | 19:00 | Bolton Wanderers Men | | Union FC Men |
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| Sun | Sep 7 | MJW | Fountain St Soccer Complex #4 (Grass) | 15:00 | Cambridge United Men | | Prostars FC MJ |
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| Sun | Sep 7 | MJE | LAmoreaux #1 | 19:00 | Black Tigers FC | | CTSA Titans |
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| Sun | Sep 7 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Burlington Bayhawks Men |
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| Sun | Sep 7 | MPW | Meadowvale Park | 14:00 | Ebony Jrs | | Croatia Norval |
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| Sun | Sep 7 | MRS | Meadowvale Park | 18:30 | Prostars FC RS | | Sporting Club Ideal De Brampton |
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| Sun | Sep 7 | MJC | Rainbow Creek | 17:00 | No Finish Football Club | | YJ Atletico FC Black |
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| Sun | Sep 7 | MJE | St. Robs CHS | 17:00 | Pana 2.0 | | Scarboro Azzurri Blues MJE |
