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| MElite | Jun 20 | Olimpia Toronto Elite | Guelph Royals Elite | Niklas BAUER | Player | Guelph Royals Elite |
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| MElite | Jun 20 | Scarboro Azzurri Blues Elite | GS United Men Elite | Atif ALI | Player | GS United Men Elite |
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| MElite | Jun 20 | Lakeshore United | Peniche CC | Tamara ODUSHU | Player | Lakeshore United |
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| MPW | Jun 20 | Fort Erie Sting | Mississauga Croatia Men | Ian DUNNE | Player | Fort Erie Sting |
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| MElite | Jun 20 | Woodbridge Strikers Men Elite | Hrvat St. Catharines | Daniel ALONZI | Player | Woodbridge Strikers Men Elite |
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| MRS | Jun 21 | Atletico Sporting Toronto Men | Prostars FC RS | Anthony AMELAWE | Player | Atletico Sporting Toronto Men |
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| MRS | Jun 21 | Atletico Sporting Toronto Men | Prostars FC RS | Oscar GARCIA | Player | Atletico Sporting Toronto Men |
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| M21RC | Jun 21 | CFC Black U21M | NY Academy U21M RC | Mohammed OMAR | Player | CFC Black U21M |
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| M21RC | Jun 21 | CFC Black U21M | NY Academy U21M RC | Christian SHARADY | Player | NY Academy U21M RC |
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| M21RC | Jun 22 | Barrie Spirit U21M | Bolton Wanderers White U21M | Daniel IPPOLITO | Player | Barrie Spirit U21M |
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| MRCE | Jun 22 | East York Men | Magic AC | Mani HAMEDANI | Player | Magic AC |
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| M21RC | Jun 22 | Bradford Wolves U21M | Atletico Sporting Toronto U21M | Abubaker FARAKAN | Player | Atletico Sporting Toronto U21M |
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| M21RC | Jun 22 | Bradford Wolves U21M | Atletico Sporting Toronto U21M | Ebrahim TATRSOU | Player | Bradford Wolves U21M |
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| MPE | Jun 22 | Scarborough Rangers | Barrie Blazers Men | Liam SPURR | Player | Barrie Blazers Men |
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| MPE | Jun 22 | Scarborough Rangers | Barrie Blazers Men | Sevin YOUZEIR | Player | Barrie Blazers Men |
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| MElite | Jun 22 | GS United Men Elite | Vaughan Azzurri Men Elite | Atif ALI | Player | GS United Men Elite |
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| MJC | Jun 23 | IFC Men | Barrie Spirit Men | Julian CAPPADOCIA | Player | IFC Men |
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| MJC | Jun 23 | IFC Men | Barrie Spirit Men | Lucas RODRIGUES | Player | IFC Men |
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| MJC | Jun 23 | IFC Men | Barrie Spirit Men | Antonio SLAYBE | Player | IFC Men |
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| MRCE | Jun 23 | GS Vets | Scarborough Town FC Men | Kevin CHRISTIE | Player | Scarborough Town FC Men |
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| M21PS | Jun 23 | SC Toronto Eagles U21M | Distinctionz U21M | Ryan ELLIS | Player | Distinctionz U21M |
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| M21RC | Jun 24 | Vaughan Azzurri U21M RC | Barrie Spirit U21M | Daniel IPPOLITO | Player | Barrie Spirit U21M |
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| M21RC | Jun 24 | Bolton Wanderers White U21M | Bradford Wolves U21M | Ebrahim TATRSOU | Player | Bradford Wolves U21M |
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| M21PC | Jun 24 | Vaughan Azzurri U21M PC | Oak Ridges Knights U21M | Adriano ANDONOFF | Player | Oak Ridges Knights U21M |
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| M21PC | Jun 24 | Vaughan Azzurri U21M PC | Oak Ridges Knights U21M | Matthew SAMMAN | Player | Oak Ridges Knights U21M |
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| MJC | Jun 25 | Toronto Irish FC II | Aurora Lions | Colin KILNER | Player | Aurora Lions |
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| M21RCE | Jun 25 | King City Royals U21M | Jarvis SC U21M | Thanush ARULANANTHAM | Player | Jarvis SC U21M |
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| M21PS | Jun 25 | Croatia Norval U21M | KNSC Lions U21M | Luis CENTENO | Player | KNSC Lions U21M |
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| M21RC | Jun 25 | Glen Shields Juventus U21M | NY Academy U21M RC | Ibrahim ELZAYAT | Player | Glen Shields Juventus U21M |
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| M21RC | Jun 25 | Glen Shields Juventus U21M | NY Academy U21M RC | ALEXANDER ROGOZOVSKI | Player | Glen Shields Juventus U21M |
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| M21RC | Jun 25 | Glen Shields Juventus U21M | NY Academy U21M RC | Christian SHARADY | Player | NY Academy U21M RC |
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| WRC | Jun 26 | King City Royals Women RC | Pickering FC Women | Daelyn TULLOCH | Player | Pickering FC Women |
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| WProv | Jun 26 | Union FC Women | King City Royals Women Prov | Francesca GIRARDO | Player | Union FC Women |
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| MPW | Jun 27 | Fort Erie Sting | AC Diavoli | Ian DUNNE | Player | Fort Erie Sting |
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| M21PC | Jun 30 | Union FC U21M | Pana U21M | Nathan COLANGELO | Player | Union FC U21M |
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| M21PC | Jun 30 | Union FC U21M | Pana U21M | Angel HERNANDEZ (CALL-UP) | Player | Union FC U21M |
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| MJW | Jul 2 | International SC | Prostars FC MJ | PENNY ADEYEMI | Player | International SC |
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| M21PC | Jul 2 | Oak Ridges Knights U21M | Thornhill Bolts U21M | Adriano ANDONOFF | Player | Oak Ridges Knights U21M |
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| M21PC | Jul 2 | Oak Ridges Knights U21M | Thornhill Bolts U21M | Matthew SAMMAN | Player | Oak Ridges Knights U21M |
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| WProv | Jul 3 | West Rouge Storm Prov | Union FC Women | Francesca GIRARDO | Player | Union FC Women |
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| WRCE | Jul 3 | Pickering FC Women | West Rouge Storm White | Daelyn TULLOCH | Player | Pickering FC Women |
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| MJC | Jul 4 | YJ Atletico FC Black | IFC Men | Julian CAPPADOCIA | Player | IFC Men |
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| MJC | Jul 4 | YJ Atletico FC Black | IFC Men | Antonio SLAYBE | Player | IFC Men |
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| MJC | Jul 4 | Aurora Lions | Newmarket United Men | Colin KILNER | Player | Aurora Lions |
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| MJW | Jul 4 | Woodbridge Strikers Men MJ | GTA United | Inder THIND | Player | GTA United |
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| MJW | Jul 4 | Woodbridge Strikers Men MJ | GTA United | Jacob KLEIN | Player | Woodbridge Strikers Men MJ |
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| M21RC | Jul 5 | NY Academy U21M RC | Barrie Spirit U21M | Daniel IPPOLITO | Player | Barrie Spirit U21M |
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| MPE | Jul 8 | Queens Park Rangers PE | Barrie Blazers Men | Liam SPURR | Player | Barrie Blazers Men |
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| MPE | Jul 8 | Queens Park Rangers PE | Barrie Blazers Men | Sevin YOUZEIR | Player | Barrie Blazers Men |
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| MJW | Jul 10 | Georgetown Mustangs Men | Woodbridge Strikers Men MJ | Jacob KLEIN | Player | Woodbridge Strikers Men MJ |
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| MPE | Jul 10 | RH PARS FC PE | Toronto Pamir | Esi GHASSEMI | Player | Toronto Pamir |
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| MPE | Jul 10 | RH PARS FC PE | Toronto Pamir | Waqas UMAR | Player | Toronto Pamir |
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| MPE | Jul 11 | Barrie Blazers Men | Aurora Hearts | Sevin YOUZEIR | Player | Barrie Blazers Men |
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| MJC | Jul 11 | Aurora Lions | RH PARS FC MJ | Colin KILNER | Player | Aurora Lions |
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| MJW | Jul 13 | Prostars FC MJ | GTA United | Inder THIND | Player | GTA United |
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| MPE | Jul 13 | Toronto Pamir | Scarborough Rangers | Esi GHASSEMI | Player | Toronto Pamir |
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| MPE | Jul 13 | Toronto Pamir | Scarborough Rangers | Waqas UMAR | Player | Toronto Pamir |
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| MJC | Jul 14 | IFC Men | Toronto Irish FC II | Julian CAPPADOCIA | Player | IFC Men |
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| MJC | Jul 14 | IFC Men | Toronto Irish FC II | Antonio SLAYBE | Player | IFC Men |
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| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Esi GHASSEMI | Player | Toronto Pamir |
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| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Waqas UMAR | Player | Toronto Pamir |
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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 |
