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| Mon | Aug 17 | M21PC | Berczy Park North | 21:00 | Jarvis SC U21M | 0 - 2 | Power FC U21M |
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| Mon | Aug 17 | MJE | Cornell CC | 21:00 | Markham Lightning Men | 3 - 4 | Newmarket United Men |
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| Mon | Aug 17 | MRS | Edelweiss Soccer Park 4-R2 | 21:00 | Bolton Wanderers White Men RS | 3 - 0 | Atletico Sporting Toronto Men |
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| Mon | Aug 17 | WRCE | Fleming PYSC East Turf | 21:00 | Cavan FC Women | 0 - 5 | Oshawa Kicks Red |
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| Mon | Aug 17 | WOpCup | LAmoreaux #1 | 21:10 | GS United W Prov | 1 - 3 | Toronto Azzurri |
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| Mon | Aug 17 | WProv | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Women | 3 - 0 | Alliance FC Mustangs Women |
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| Mon | Aug 17 | WRC | St. Joan of Arc | 21:00 | DFC Union Women | 3 - 2 | KNSC Lions Women |
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| Tue | Aug 18 | WRSW | Fountain St Soccer Complex #4 (Grass) | 21:00 | Cambridge United Women | 1 - 3 | Woodstock FC Women |
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| Tue | Aug 18 | WRS | Joe Sams (Leisureplex) Field 2 | 21:00 | Flamborough Dundas | 0 - 1 | Rockwood FC Black |
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| Tue | Aug 18 | MPE | LAmoreaux #1 | 21:00 | QPR PE | 2 - 1 | North York Hearts |
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| Tue | Aug 18 | M21RCE | LAmoreaux #5 | 19:00 | The SA U21M | 3 - 1 | GS United U21M |
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| Tue | Aug 18 | MRS | Nora Frances Henderson Football Field | 21:00 | Globe FC | 3 - 3 | Prostars FC |
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| Tue | Aug 18 | MElite | North Maple Regional Park Turf #1 | 21:00 | Vaughan Azzurri Elite | 5 - 1 | Peniche CC |
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| Tue | Aug 18 | M21PS | St. Francis Xavier Catholic SS Milton | 21:00 | Scrosoppi FC U21M | 0 - 1 | USC Karpaty U21M |
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| Tue | Aug 18 | MJW | Trafalgar Sports Park 10 | 21:00 | Georgetown Mustangs Men | 2 - 3 | Distinctionz Men MJ |
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| Tue | Aug 18 | M21RC | William Neal Park | 19:00 | Oak Ridges Knights U21M RC | 9 - 0 | KNSC Lions U21M |
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| Wed | Aug 19 | WRCE | Centennial College | 21:00 | West Rouge Storm Black | 0 - 6 | Pickering FC Women |
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| Wed | Aug 19 | MRC | Centennial Park 2 Etobicoke (11v11) | 21:00 | USC Karpaty Men RC | 7 - 0 | SC Toronto Eagles Men |
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| Wed | Aug 19 | WRC | Cherry Beach West | 21:00 | SC Toronto Eagles Women | 1 - 0 | Olimpia Toronto Women |
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| Wed | Aug 19 | MJW | Earlscourt North | 21:00 | Toronto Irish FC II | 0 - 0 | CFC Atletico Black |
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| Wed | Aug 19 | MOpCup | LAmoreaux #1 | 21:05 | GS United Men | 5 - 3 | Distinctionz Men PW |
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| Wed | Aug 19 | MRCE | LAmoreaux #5 | 21:10 | Scarborough Town FC RCE | 2 - 2 | QPR Reg |
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| Wed | Aug 19 | WRCE | Major Abbas Ali Park East | 21:00 | GS United W Reg | 0 - 3 | Oshawa Kicks White |
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| Wed | Aug 19 | WRSW | Marden Park 1 | 21:00 | Rockwood FC Blue | 3 - 1 | Kitchener TFC Grey |
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| Wed | Aug 19 | WRC | South Common | 21:00 | Mississauga Croatia Women | 5 - 6 | KNSC Lions Women |
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| Wed | Aug 19 | WRC | St. Joan of Arc | 21:00 | DFC Union Women | 0 - 2 | UMSC Women |
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| Wed | Aug 19 | M21RC | Villanova Turf | 21:00 | DFC Union Navy U21M | 3 - 2 | King City Royals U21M |
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| Thu | Aug 20 | WProv | Caledon R3 | 21:00 | Caledon United FC W Prov | 3 - 0 | Newmarket United W Prov |
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| Thu | Aug 20 | MRS | Centennial Bowl Guelph | 21:00 | Guelph Royals RS | 2 - 0 | Clarkson SC |
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| Thu | Aug 20 | MJE | Centennial College Scarborough | 21:00 | Scarborough Town FC MJ | 0 - 3 | PFC Galacticos |
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| Thu | Aug 20 | MPE | David Hamilton | 21:00 | RH PARS FC | 4 - 0 | SPG Red Devils United |
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| Thu | Aug 20 | WRSW | Fountain St Soccer Complex #4 (Grass) | 21:00 | Cambridge United Women | 0 - 3 | Banat FC |
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| Thu | Aug 20 | MJE | LAmoreaux #5 | 21:00 | Scarboro Azzurri Blues MJ | 0 - 7 | Stouffville Mustangs Yellow |
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| Thu | Aug 20 | WRS | Marden Park 1 | 21:00 | Rockwood FC Black | 1 - 0 | Gryphons FC Women |
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| Thu | Aug 20 | MPW | Orchard Park SS | 20:00 | Hamilton Serbians | 1 - 2 | Burlington Bayhawks |
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| Thu | Aug 20 | MRC | Rob Ford Stadium | 19:00 | Magic AC | 0 - 3 | Bradford Wolves |
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| Thu | Aug 20 | MElite | Southward 1 - 11v11 | 20:45 | Hrvat St. Catharines | 2 - 0 | Toronto Celtic |
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| Thu | Aug 20 | WProv | Villanova Turf | 21:00 | King City Royals Women | 1 - 0 | Toronto Azzurri |
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| Fri | Aug 21 | MJE | Barrie SC Development Centre | 21:00 | Barrie Blazers Men MJ | 8 - 1 | DFC Union Men |
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| Fri | Aug 21 | MJE | Bethesda #1 | 21:00 | Stouffville Mustangs Blue | 5 - 1 | Ajax SC |
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| Fri | Aug 21 | MJE | Keelesdale | 21:00 | CFC Atletico Blue | 4 - 0 | FCD Aces |
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| Fri | Aug 21 | MRCE | LAmoreaux #1 | 21:00 | Olympiakos SC | 2 - 0 | Peterborough City Men |
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| Fri | Aug 21 | MOpCup | Paramount Fine Foods Centre 1 | 21:00 | Olimpia Elite | 4 - 2 | Scarboro Azzurri Blues Elite |
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| Fri | Aug 21 | MPE | Vaughan Grove 1 | 21:15 | Woodbridge Strikers Men | 3 - 2 | Cavan FC Men |
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| Fri | Aug 21 | MPW | Victoria Park Brampton | 21:00 | Sporting Club Ideal De Brampton | | Distinctionz Men PW |
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| Fri | Aug 21 | MJW | York University Grass | 21:00 | FC E Etobicoke United FC | 3 - 0 | USC Karpaty Men MJW |
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| Sat | Aug 22 | MJW | Brickyard | 18:00 | Toronto Tigers AST | | PRP FC |
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| Sat | Aug 22 | WRCE | Monarch Park North Grass (Ajax) | 16:30 | PFC Valkyries | | GS United W Reg |
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| Sat | Aug 22 | M21RC | Sir William Mulock - Newmarket | 15:00 | DFC Union Navy U21M | 5 - 2 | Oak Ridges Knights U21M RC |
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| Sun | Aug 23 | MRCE | Beverley Morgan Park | 19:00 | QPR Reg | | Peterborough City Men |
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| Sun | Aug 23 | MRS | Brickyard | 16:00 | Olimpia Toronto II | | Bolton Wanderers White Men RS |
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| Sun | Aug 23 | MJW | Brickyard | 20:00 | Distinctionz Men MJ | | Atletico Toronto |
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| Sun | Aug 23 | M21RSW | Campo Do Oriental | 17:00 | Oriental SC U21M | | Hamilton Croatia U21M |
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| Sun | Aug 23 | MPW | Chris Gibson Park 1 | 14:30 | Ebony Jrs | | Lakeshore United |
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| Sun | Aug 23 | MElite | Christ The King CSS | 18:00 | Croatia Norval Men | | Peniche CC |
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| Sun | Aug 23 | M21PS | Citywide Field #2 | 20:00 | Whitecaps London U21M | | USC Karpaty U21M |
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| Sun | Aug 23 | MRCE | Dieppe Park | 16:00 | East York Men | | Scarborough Town FC RCE |
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| Sun | Aug 23 | M21PC | Earlscourt North | 09:00 | NY Academy U21M | | GFC Juve U21M |
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| Sun | Aug 23 | MRC | Henderson Park East | 18:00 | Bradford Wolves | | KNSC Lions Men |
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| Sun | Aug 23 | MJW | Humberview SS | 18:00 | Caledon United FC Men | | Paris FC |
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| Sun | Aug 23 | WRC | Keelesdale | 21:00 | CFC Atletico Women | | NYC Panthers |
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| Sun | Aug 23 | MElite | LAmoreaux #1 | 19:00 | Panathinaikos | | Guelph Royals Elite |
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| Sun | Aug 23 | MElite | LAmoreaux #1 | 21:10 | GS United Men | | Vaughan Azzurri Elite |
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| Sun | Aug 23 | MRCE | LAmoreaux #5 | 19:00 | Artemisium FC | | Scarborough Rangers |
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| Sun | Aug 23 | M21PC | LAmoreaux #5 | 21:00 | Olympiacos Toronto K21 | | Oak Ridges Knights U21M Prov |
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| Sun | Aug 23 | MRS | Meadowvale (Syntex) | 18:00 | Prostars FC | | GTA United |
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| Sun | Aug 23 | MPW | Meadowvale (Syntex) | 20:45 | AC Diavoli | | Mississauga Croatia Men |
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| Sun | Aug 23 | WRC | Nottawasaga Inn #1 | 16:00 | Nottawasaga FC | | Newmarket United II W |
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| Sun | Aug 23 | MJE | Richmond Green West | 17:00 | Richmond Hill Raiders | | PFC Galacticos |
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| Sun | Aug 23 | MRC | Save Max Sports Centre Field 1 | 18:30 | No Finish FC | | Magic AC |
