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| MJC | May 30 | YJ Atletico FC Black | Barrie Spirit Men | Ollie HOGAN | Player | Barrie Spirit Men |
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| MPW | May 30 | Mississauga Croatia Men | Ebony Jrs | Tyrece HARRISON | Player | Ebony Jrs |
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| MPW | May 30 | Mississauga Croatia Men | Ebony Jrs | Kareem HAWES | Player | Ebony Jrs |
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| MPW | May 30 | Mississauga Croatia Men | Ebony Jrs | Matthew DA SILVA | Player | Mississauga Croatia Men |
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| M21PC | May 31 | NY Academy U21M PC | Vaughan Azzurri U21M PC | GABRIEL ETIENNE | Player | Vaughan Azzurri U21M PC |
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| M21PC | May 31 | NY Academy U21M PC | Vaughan Azzurri U21M PC | DAVID RAO | Player | Vaughan Azzurri U21M PC |
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| MRC | May 31 | Union FC Men | KNSC Lions Men | Dennis AGUIRRE | Player | Union FC Men |
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| MPW | May 31 | Distinctionz Men | Fort Erie Sting | Massimo BUSCEMA | Player | Fort Erie Sting |
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| MPW | May 31 | Distinctionz Men | Fort Erie Sting | Ian DUNNE | Player | Fort Erie Sting |
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| MRS | Jun 1 | Olimpia Toronto II | Globe FC | Stephen ARMSTRONG | Player | Olimpia Toronto II |
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| MPW | Jun 1 | AIFC Men | Croatia Norval | Hakeem BAILEY | Player | AIFC Men |
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| MPW | Jun 1 | AIFC Men | Croatia Norval | Oliver TOLO | Player | Croatia Norval |
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| MRCE | Jun 1 | Artemisium FC | Magic AC | Nicoy MONTIQUE | Player | Magic AC |
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| MJE | Jun 2 | YJ Atletico FC Blue | Black Tigers FC | Roshan RAJAKULAM | Player | Black Tigers FC |
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| MJE | Jun 2 | YJ Atletico FC Blue | Black Tigers FC | Mir Asfar AHMED | Player | YJ Atletico FC Blue |
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| MPE | Jun 3 | Toronto Celtic | Scarborough Rangers | Vithunan SIVAKUMAR | Player | Scarborough Rangers |
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| M21PC | Jun 4 | Oak Ridges Knights U21M | Pickering FC U21M | Panayiotis BABALIS | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 4 | Oak Ridges Knights U21M | Pickering FC U21M | Adamo MASTRANGELI | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 4 | Oak Ridges Knights U21M | Pickering FC U21M | Matt PASSACQUALE | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 4 | Union FC U21M | Pana U21M | Nathan COLANGELO | Player | Union FC U21M |
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| M21PC | Jun 4 | Union FC U21M | Pana U21M | Angel HERNANDEZ (CALL-UP) | Player | Union FC U21M |
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| MRC | Jun 4 | Toronto Irish FC | USC Karpaty Men | Kevin THENADEY | Player | Toronto Irish FC |
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| MRC | Jun 4 | Toronto Irish FC | USC Karpaty Men | Pavlo KHOMA | Player | USC Karpaty Men |
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| MRCE | Jun 4 | Scarborough Town FC Men | Magic AC | Nicoy MONTIQUE | Player | Magic AC |
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| MRS | Jun 5 | Hamilton Serbians | Guelph Royals RS | Ethan GLASCOTT | Player | Guelph Royals RS |
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| MJE | Jun 5 | CTSA Titans | Black Tigers FC | Roshan RAJAKULAM | Player | Black Tigers FC |
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| MPE | Jun 6 | Barrie Blazers Men | RH PARS FC PE | Tufan NOORFEKANTASMALOU | Player | RH PARS FC PE |
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| MElite | Jun 6 | Olimpia Toronto Elite | Panathinaikos Elite | Chris NAJDIENOW | Player | Olimpia Toronto Elite |
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| MPE | Jun 6 | Aurora Hearts | Scarborough Rangers | Vithunan SIVAKUMAR | Player | Scarborough Rangers |
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| M21PC | Jun 7 | Olympiacos Toronto K21 | Vaughan Azzurri U21M PC | DAVID RAO | Player | Vaughan Azzurri U21M PC |
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| MJE | Jun 7 | Ajax Galacticos | Markham Lightning | Adrian BAROVIER | Player | Markham Lightning |
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| MJE | Jun 7 | Ajax Galacticos | Markham Lightning | Ethan BROWNE | Player | Markham Lightning |
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| MJE | Jun 7 | Ajax Galacticos | Markham Lightning | Liam THURSFIELD | Player | Markham Lightning |
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| M21RCE | Jun 8 | Olympic Flame K19 | The Scarborough Academy U21M | Lucas KESTELIDIS | Player | Olympic Flame K19 |
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| M21RC | Jun 8 | Barrie Spirit U21M | Atletico Sporting Toronto U21M | Roy ONE | Player | Atletico Sporting Toronto U21M |
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| MRS | Jun 8 | Olimpia Toronto II | Prostars FC RS | Stephen ARMSTRONG | Player | Olimpia Toronto II |
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| MPW | Jun 8 | Croatia Norval | Mississauga Croatia Men | Matthew DA SILVA | Player | Mississauga Croatia Men |
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| MJE | Jun 8 | Black Tigers FC | Pana 2.0 | Roshan RAJAKULAM | Player | Black Tigers FC |
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| MJE | Jun 11 | Markham Lightning | Peterborough City Men MJE | Adrian BAROVIER | Player | Markham Lightning |
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| MJE | Jun 11 | Markham Lightning | Peterborough City Men MJE | Ethan BROWNE | Player | Markham Lightning |
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| MJE | Jun 11 | Markham Lightning | Peterborough City Men MJE | Liam THURSFIELD | Player | Markham Lightning |
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| M21PC | Jun 11 | Union FC U21M | Pickering FC U21M | Nathan COLANGELO | Player | Union FC U21M |
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| M21PC | Jun 11 | Union FC U21M | Pickering FC U21M | Angel HERNANDEZ (CALL-UP) | Player | Union FC U21M |
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| M21PC | Jun 14 | NY Academy U21M PC | Oak Ridges Knights U21M | Panayiotis BABALIS | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 14 | NY Academy U21M PC | Oak Ridges Knights U21M | Matt PASSACQUALE | Player | Oak Ridges Knights U21M |
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| MJE | Jun 16 | YJ Atletico FC Blue | Markham Lightning | Adrian BAROVIER | Player | Markham Lightning |
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| M21PC | Jun 18 | Oak Ridges Knights U21M | Pana U21M | Panayiotis BABALIS | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 18 | Oak Ridges Knights U21M | Pana U21M | Matt PASSACQUALE | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 22 | Thornhill Bolts U21M | Union FC U21M | Nathan COLANGELO | Player | Union FC U21M |
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| M21PC | Jun 22 | Thornhill Bolts U21M | Union FC U21M | Angel HERNANDEZ (CALL-UP) | Player | Union FC U21M |
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| WRC | Aug 21 | Bradford Wolves Women | Aurora Spurs | Natalia CASIELLO | Player | Bradford Wolves Women |
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| M21RC | Aug 24 | CFC Black U21M | Atletico Sporting Toronto U21M | Roy ONE | Player | Atletico Sporting Toronto U21M |
