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| MJW | Jul 12 | Caledon United FC Men | FC E Etobicoke United FC | Shakeem KELLMAN | Player | FC E Etobicoke United FC |
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| MJW | Jul 12 | Caledon United FC Men | FC E Etobicoke United FC | Thomas VELEZ | Player | FC E Etobicoke United FC |
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| MElite | Jul 12 | Panathinaikos | Croatia Norval Men | Chris Maniatis | Coach | Panathinaikos |
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| M21RSW | Jul 12 | Woodstock FC U21M | Waterloo United U21M | Lockhart EVAN | Player | Woodstock FC U21M |
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| MJW | Jul 12 | Paris FC | USC Karpaty Men MJW | Hunter BROUILLARD | Player | Paris FC |
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| MJW | Jul 12 | Paris FC | USC Karpaty Men MJW | Rowen PILKINGTON | Player | Paris FC |
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| MJW | Jul 12 | Paris FC | USC Karpaty Men MJW | Ashton SPIVAK | Player | Paris FC |
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| MJW | Jul 12 | Paris FC | USC Karpaty Men MJW | Vitalii DUMENKO | Player | USC Karpaty Men MJW |
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| MJW | Jul 12 | Paris FC | USC Karpaty Men MJW | Genti GASHI | Player | USC Karpaty Men MJW |
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| MJW | Jul 12 | Distinctionz Men MJ | Toronto Tigers AST | Zakaria LAFEL | Player | Toronto Tigers AST |
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| M21RC | Jul 12 | Barrie Spirit U21M | DFC Union Navy U21M | Jaydan GIORDANO | Player | Barrie Spirit U21M |
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| M21RS | Jul 13 | SSE 90 U21M | SC Toronto Eagles U21M | Angad SOHI | Player | SSE 90 U21M |
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| MPE | Jul 13 | North York Hearts | QPR PE | Alex DE CAROLIS | Player | North York Hearts |
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| M21RCE | Jul 13 | Whitby FC U21M | The SA U21M | Savion SMITH | Player | Whitby FC U21M |
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| MRS | Jul 14 | Globe FC | Clarkson SC | Joshua PORTILLO | Player | Clarkson SC |
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| MElite | Jul 14 | Peniche CC | Olimpia Elite | Joao Renato FREITAS | Player | Peniche CC |
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| MElite | Jul 14 | Peniche CC | Olimpia Elite | Jordan PEREIRA | Player | Peniche CC |
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| M21PS | Jul 15 | Dixie U21M | Croatia Norval U21M | Joel DE OLIVERA | Player | Dixie U21M |
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| M21PS | Jul 15 | Dixie U21M | Croatia Norval U21M | Zaharije JEFTIC | Player | Dixie U21M |
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| M21PS | Jul 15 | Dixie U21M | Croatia Norval U21M | Christopher JOSEPH | Player | Dixie U21M |
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| M21RC | Jul 15 | King City Royals U21M | Barrie Spirit U21M | Jaydan GIORDANO | Player | Barrie Spirit U21M |
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| W21RCE | Jul 16 | NYFC Strikers U21W | East York U21W | Iliana LOREFICE | Player | East York U21W |
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| M21RS | Jul 16 | NT Nitros U21M | DFC Union Orange U21M | Artyom ANTSUPOV | Player | DFC Union Orange U21M |
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| M21RS | Jul 16 | NT Nitros U21M | DFC Union Orange U21M | Caden JONES | Player | DFC Union Orange U21M |
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| M21RS | Jul 16 | NT Nitros U21M | DFC Union Orange U21M | Gabriel KHOUNGANIAN | Player | DFC Union Orange U21M |
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| MRCE | Jul 16 | Pana 2.0 | Olympiakos SC | Adeen CHIN | Player | Olympiakos SC |
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| MRS | Jul 16 | Guelph Royals RS | Prostars FC | Marcus SIMMS | Player | Guelph Royals RS |
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| MRS | Jul 16 | Guelph Royals RS | Prostars FC | Lucas VANSTONE | Player | Prostars FC |
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| MJW | Jul 17 | Bolton Wanderers Blue Men | CFC Atletico White | Akeem OPANIRAN | Player | CFC Atletico White |
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| MJW | Jul 17 | Bolton Wanderers Blue Men | CFC Atletico White | Marcus QUIJANO | Player | CFC Atletico White |
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| MJW | Jul 17 | FC E Etobicoke United FC | Atletico Toronto | Shakeem KELLMAN | Player | FC E Etobicoke United FC |
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| MJW | Jul 17 | FC E Etobicoke United FC | Atletico Toronto | Thomas VELEZ | Player | FC E Etobicoke United FC |
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| MJW | Jul 17 | CFC Atletico Black | Caledon United FC Men | Ahamed HASSKA | Player | CFC Atletico Black |
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| MJW | Jul 17 | CFC Atletico Black | Caledon United FC Men | Danzyl KAIZEMI | Player | CFC Atletico Black |
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| MJW | Jul 17 | CFC Atletico Black | Caledon United FC Men | Stavros ZINDROS | Player | CFC Atletico Black |
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| M21RCE | Jul 17 | Cavan FC U21M | Whitby FC U21M | Savion SMITH | Player | Whitby FC U21M |
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| MPW | Jul 17 | Mississauga Croatia Men | AC Diavoli | Zachary MACLEAN SZWEZ | Player | AC Diavoli |
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| MPW | Jul 17 | Mississauga Croatia Men | AC Diavoli | Alen MIJACKOVIC | Player | Mississauga Croatia Men |
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| MPE | Jul 17 | Woodbridge Strikers Men | Toronto Pamir | Marco RODRIGUEZ | Player | Woodbridge Strikers Men |
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| MJE | Jul 18 | FCD Aces | Newmarket United Men | Sharafuddin MEHRZAI | Player | FCD Aces |
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| MRS | Jul 18 | Atletico Sporting Toronto Men | Clarkson SC | Joshua PORTILLO | Player | Clarkson SC |
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| W21RCE | Jul 19 | GFA Yellow | East York U21W | Iliana LOREFICE | Player | East York U21W |
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| M21RCE | Jul 20 | Whitby FC U21M | Asante Elite U21M | Savion SMITH | Player | Whitby FC U21M |
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| M21RS | Jul 20 | SC Toronto Eagles U21M | Georgetown Mustangs U21M | Ali RAUF | Player | Georgetown Mustangs U21M |
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| M21PS | Jul 22 | Dixie U21M | Scrosoppi FC U21M | Joel DE OLIVERA | Player | Dixie U21M |
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| M21PS | Jul 22 | Dixie U21M | Scrosoppi FC U21M | Zaharije JEFTIC | Player | Dixie U21M |
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| M21PS | Jul 22 | Dixie U21M | Scrosoppi FC U21M | Christopher JOSEPH | Player | Dixie U21M |
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| M21RS | Jul 22 | DFC Union Orange U21M | SSE 90 U21M | Caden JONES | Player | DFC Union Orange U21M |
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| M21RS | Jul 23 | NT Nitros U21M | Georgetown Mustangs U21M | Ali RAUF | Player | Georgetown Mustangs U21M |
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| WRC | Jul 23 | UMSC Women | CFC Atletico Women | Taylor DREW | Player | CFC Atletico Women |
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| MJW | Jul 24 | CFC Atletico Black | CFC Atletico White | Ahamed HASSKA | Player | CFC Atletico Black |
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| MJW | Jul 24 | CFC Atletico Black | CFC Atletico White | Stavros ZINDROS | Player | CFC Atletico Black |
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| MJW | Jul 24 | CFC Atletico Black | CFC Atletico White | Akeem OPANIRAN | Player | CFC Atletico White |
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| MJW | Jul 24 | CFC Atletico Black | CFC Atletico White | Marcus QUIJANO | Player | CFC Atletico White |
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| MJW | Jul 25 | USC Karpaty Men MJW | Caledon United FC Men | Genti GASHI | Player | USC Karpaty Men MJW |
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| MRS | Jul 26 | Prostars FC | Bolton Wanderers White Men RS | Lucas VANSTONE | Player | Prostars FC |
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| M21RSW | Jul 26 | Cambridge United U21M | Woodstock FC U21M | Lockhart EVAN | Player | Woodstock FC U21M |
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| MJW | Jul 26 | Paris FC | Toronto Irish FC II | Hunter BROUILLARD | Player | Paris FC |
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| MJW | Jul 26 | Paris FC | Toronto Irish FC II | Rowen PILKINGTON | Player | Paris FC |
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| M21RS | Jul 28 | Georgetown Mustangs U21M | DFC Union Orange U21M | Caden JONES | Player | DFC Union Orange U21M |
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| MJE | Jul 28 | DFC Union Men | FCD Aces | Sharafuddin MEHRZAI | Player | FCD Aces |
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| M21RSW | Jul 29 | Eagles 1982 U21M | Woodstock FC U21M | Lockhart EVAN | Player | Woodstock FC U21M |
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| MElite | Jul 30 | Hrvat St. Catharines | Peniche CC | Joao Renato FREITAS | Player | Peniche CC |
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| M21RC | Jul 31 | DFC Union Navy U21M | IFC U21M | Winfred SARPONG | Player | DFC Union Navy U21M |
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| MJW | Aug 7 | FC E Etobicoke United FC | CFC Atletico White | Marcus QUIJANO | Player | CFC Atletico White |
|
| MJW | Aug 8 | USC Karpaty Men MJW | CFC Atletico Black | Ahamed HASSKA | Player | CFC Atletico Black |
|
| MJW | Aug 8 | USC Karpaty Men MJW | CFC Atletico Black | Genti GASHI | Player | USC Karpaty Men MJW |
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| MJW | Aug 9 | Paris FC | FC E Etobicoke United FC | Hunter BROUILLARD | Player | Paris FC |
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| MJW | Aug 9 | Paris FC | FC E Etobicoke United FC | Rowen PILKINGTON | Player | Paris FC |
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| M21RC | Aug 22 | DFC Union Navy U21M | Oak Ridges Knights U21M RC | Winfred SARPONG | Player | DFC Union Navy U21M |
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| WRC | Aug 27 | KNSC Lions Women | CFC Atletico Women | Taylor DREW | Player | CFC Atletico Women |
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| MJE | Sep 2 | Markham Lightning Men | Scarborough Town FC MJ | Michael MAZZUCA | Player | Markham Lightning Men |
