| M21PC | Jul 11 | Thornhill Bolts U21M | Union FC U21M | Nathan COLANGELO | Player | Union FC U21M |
| M21PC | Jul 11 | Thornhill Bolts U21M | Union FC U21M | Angel HERNANDEZ (CALL-UP) | Player | Union FC U21M |
| M21PC | Jul 11 | Thornhill Bolts U21M | Union FC U21M | Matthew YOUT | Player | Union FC U21M |
| M21RS | Jul 11 | Gryphons FC U21M | Dixie SC U21M | Christopher JOSEPH | Player | Dixie SC U21M |
| MElite | Jul 11 | Woodbridge Strikers Men Elite | Peniche CC | Daniel PEREIRA | Player | Woodbridge Strikers Men Elite |
| M21RC | Jul 12 | NY Academy U21M RC | Vaughan Azzurri U21M RC | Samuel KABWIKA | Player | Vaughan Azzurri U21M RC |
| M21RS | Jul 12 | Toronto United FC U21M | Mississauga Croatia U21M | Iranzi CHRIST | Player | Toronto United FC U21M |
| M21PS | Jul 12 | KNSC Lions U21M | USC Karpaty U21M | Peter LOZINSKYY | Player | USC Karpaty U21M |
| M21PS | Jul 12 | KNSC Lions U21M | USC Karpaty U21M | Julian PETRUK | Player | USC Karpaty U21M |
| M21RC | Jul 12 | Atletico Sporting Toronto U21M | Barrie Spirit U21M | Oriol Call UPS HUGHES | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 12 | Atletico Sporting Toronto U21M | Barrie Spirit U21M | Márquez RODRIGUEZ | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 12 | Atletico Sporting Toronto U21M | Barrie Spirit U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| MJW | Jul 13 | Prostars FC MJ | GTA United | Inder THIND | Player | GTA United |
| MPW | Jul 13 | Croatia Norval | Fort Erie Sting | Oliver TOLO | Player | Croatia Norval |
| W21RC | Jul 13 | Barrie Spirit U21W | Glen Shields Juventus U21W | Sophia TOMEI | Player | Barrie Spirit U21W |
| MPE | Jul 13 | Toronto Pamir | Scarborough Rangers | Esi GHASSEMI | Player | Toronto Pamir |
| MPE | Jul 13 | Toronto Pamir | Scarborough Rangers | Waqas UMAR | Player | Toronto Pamir |
| MElite | Jul 13 | Panathinaikos Elite | Woodbridge Strikers Men Elite | Daniel PEREIRA | Player | Woodbridge Strikers Men Elite |
| MRC | Jul 13 | KNSC Lions Men | Union FC Men | Themy AMAYA GIL | Player | Union FC Men |
| MRC | Jul 13 | KNSC Lions Men | Union FC Men | Themy AMAYA GIL | Player | Union FC Men |
| MRC | Jul 13 | KNSC Lions Men | Union FC Men | Michael BAGLIONI | Player | Union FC Men |
| MRC | Jul 13 | KNSC Lions Men | Union FC Men | Alessandro TANSELLA | Player | Union FC Men |
| WProv | Jul 14 | Vaughan Azzurri Women | Caledon United FC W Prov | Bianca CARDELLI | Player | Vaughan Azzurri Women |
| MJC | Jul 14 | IFC Men | Toronto Irish FC II | Julian CAPPADOCIA | Player | IFC Men |
| MJC | Jul 14 | IFC Men | Toronto Irish FC II | Antonio SLAYBE | Player | IFC Men |
| MJC | Jul 14 | IFC Men | Toronto Irish FC II | Daniel TSARVENKOV | Player | IFC Men |
| MRC | Jul 14 | North York Hearts | USC Karpaty Men | Markus MOLDER | Player | North York Hearts |
| MRC | Jul 14 | North York Hearts | USC Karpaty Men | Kia RADMAND | Player | North York Hearts |
| MRC | Jul 14 | North York Hearts | USC Karpaty Men | Nicholas DROBENKO | Player | USC Karpaty Men |
| M21RCE | Jul 15 | Jarvis SC U21M | King City Royals U21M | Adrian DE MELIS | Player | King City Royals U21M |
| M21RCE | Jul 15 | Jarvis SC U21M | King City Royals U21M | Christian LAURIOLA | Player | King City Royals U21M |
| M21RCE | Jul 15 | Jarvis SC U21M | King City Royals U21M | Daniel NIRO | Player | King City Royals U21M |
| M21RC | Jul 15 | Vaughan Azzurri U21M RC | Bradford Wolves U21M | Samuel KABWIKA | Player | Vaughan Azzurri U21M RC |
| MRS | Jul 15 | Globe FC | Sporting Club Ideal De Brampton | Alexander MESQUITA | Player | Globe FC |
| W21RC | Jul 16 | SC Toronto Eagles U21W | Barrie Spirit U21W | Sophia TOMEI | Player | Barrie Spirit U21W |
| WRS | Jul 16 | Mississauga Croatia Women | Georgetown Mustangs Women | Ivona EREIZ | Player | Mississauga Croatia Women |
| MJE | Jul 16 | Markham Lightning | CTSA Titans | Anthony Gaetano RUGGERO | Player | CTSA Titans |
| M21RC | Jul 16 | Atletico Sporting Toronto U21M | CFC Black U21M | Oriol Call UPS HUGHES | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 16 | Atletico Sporting Toronto U21M | CFC Black U21M | Márquez RODRIGUEZ | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 16 | Atletico Sporting Toronto U21M | CFC Black U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 16 | Atletico Sporting Toronto U21M | CFC Black U21M | Oba TAIWO | Player | CFC Black U21M |
| M21RS | Jul 16 | Dixie SC U21M | Oriental SC U21M | Christopher JOSEPH | Player | Dixie SC U21M |
| M21RS | Jul 16 | Brampton Elite U21M | Toronto United FC U21M | Iranzi CHRIST | Player | Toronto United FC U21M |
| M21PC | Jul 17 | Pana U21M | Union FC U21M | Matthew YOUT | Player | Union FC U21M |
| W21RC | Jul 18 | NYFC Strikers U21W | NT Nitros U21W | Simran Kaur GILL | Player | NYFC Strikers U21W |
| MPW | Jul 18 | Fort Erie Sting | Croatia Norval | Oliver TOLO | Player | Croatia Norval |
| M21RCE | Jul 18 | The Scarborough Academy U21M | Scarborough Town FC U21M | Anas LACHABI | Player | Scarborough Town FC U21M |
| M21RC | Jul 19 | NY Academy U21M RC | Atletico Sporting Toronto U21M | Oriol Call UPS HUGHES | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 19 | NY Academy U21M RC | Atletico Sporting Toronto U21M | Márquez RODRIGUEZ | Player | Atletico Sporting Toronto U21M |
| M21RC | Jul 19 | NY Academy U21M RC | Atletico Sporting Toronto U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| MRC | Jul 19 | Union FC Men | USC Karpaty Men | Michael BAGLIONI | Player | Union FC Men |
| MRC | Jul 19 | Union FC Men | USC Karpaty Men | Alessandro TANSELLA | Player | Union FC Men |
| MRC | Jul 19 | Union FC Men | USC Karpaty Men | Nicholas DROBENKO | Player | USC Karpaty Men |
| MJW | Jul 19 | Toronto Tigers AST | Prostars FC MJ | Bryan Vivanco | Coach | Toronto Tigers AST |
| MJC | Jul 20 | No Finish Football Club | IFC Men | Daniel TSARVENKOV | Player | IFC Men |
| W21RC | Jul 20 | Barrie Spirit U21W | Markham Lightning U21W | Sophia TOMEI | Player | Barrie Spirit U21W |
| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Thrassos Vryonides | Coach | Aurora Hearts |
| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Hugo HERNANDEZ | Player | Aurora Hearts |
| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Esi GHASSEMI | Player | Toronto Pamir |
| MPE | Jul 20 | Toronto Pamir | Aurora Hearts | Waqas UMAR | Player | Toronto Pamir |
| MRC | Jul 20 | KNSC Lions Men | North York Hearts | Markus MOLDER | Player | North York Hearts |
| MRC | Jul 20 | KNSC Lions Men | North York Hearts | Kia RADMAND | Player | North York Hearts |
| M21PC | Jul 22 | Pickering FC U21M | Union FC U21M | Matthew YOUT | Player | Union FC U21M |
| WRS | Jul 23 | Mississauga Croatia Women | Woodbridge Strikers Women | Ivona EREIZ | Player | Mississauga Croatia Women |
| MRC | Jul 25 | Bradford Wolves Men | USC Karpaty Men | Nicholas DROBENKO | Player | USC Karpaty Men |
| MPE | Jul 25 | Aurora Hearts | Queens Park Rangers PE | Thrassos Vryonides | Coach | Aurora Hearts |
| MPE | Jul 25 | Aurora Hearts | Queens Park Rangers PE | Hugo HERNANDEZ | Player | Aurora Hearts |
| MRC | Jul 26 | Union FC Men | Bolton Wanderers Men | Michael BAGLIONI | Player | Union FC Men |
| MRC | Jul 26 | Union FC Men | Bolton Wanderers Men | Alessandro TANSELLA | Player | Union FC Men |
| M21RC | Jul 27 | CFC Black U21M | West Toronto United U21M | Oba TAIWO | Player | CFC Black U21M |
| M21PS | Jul 27 | Whitecaps London U21M | USC Karpaty U21M | Peter LOZINSKYY | Player | USC Karpaty U21M |
| M21RS | Jul 27 | Oriental SC U21M | Toronto United FC U21M | Iranzi CHRIST | Player | Toronto United FC U21M |
| MPE | Jul 27 | Cavan FC Men | Aurora Hearts | Thrassos Vryonides | Coach | Aurora Hearts |
| M21RC | Jul 29 | Vaughan Azzurri U21M RC | Atletico Sporting Toronto U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| MJW | Jul 30 | International SC | Toronto Tigers AST | Bryan Vivanco | Coach | Toronto Tigers AST |
| M21RC | Aug 6 | Glen Shields Juventus U21M | Atletico Sporting Toronto U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| M21RC | Aug 9 | Atletico Sporting Toronto U21M | Bradford Wolves U21M | Austin Call UPS WATKINS | Player | Atletico Sporting Toronto U21M |
| WRC | Aug 21 | Bradford Wolves Women | Aurora Spurs | Natalia CASIELLO | Player | Bradford Wolves Women |
| M21RC | Aug 24 | CFC Black U21M | Atletico Sporting Toronto U21M | Roy ONE | Player | Atletico Sporting Toronto U21M |
| MJC | Aug 29 | Aurora Lions | RH PARS FC MJ | Colin KILNER | Player | Aurora Lions |
| MJW | Sep 26 | Woodbridge Strikers Men MJ | Toronto Tigers AST | Bryan Vivanco | Coach | Toronto Tigers AST |
| MJE | Sep 28 | CTSA Titans | Black Tigers FC | Roshan RAJAKULAM | Player | Black Tigers FC |