The 2023 season and inaugural Open Cup is underway. Best of luck to all teams!
Prize Money
1st - $5,000
2nd - $1,000
Semi-finalist - $500
1st Round
AIFC Men advance to 2nd round
2nd Round
| HOME | VISITOR | Game | ||||
| 2. | AIFC Men | 1 | vs | 0 | Clarkson Comets | Monday May 8 - 7:00pm Ontario Soccer Centre |
| 3. | Union FC MJ | 4 | vs | 3 | Artemisium | Monday May 8 – 9:00pm Ontario Soccer Centre |
| 4. | Ebony Jrs | 3 | vs | 1 | Asante Elite | Tuesday May 9 – 7:00pm Ontario Soccer Centre |
| 5. | Rustic AC | 0 | vs | 2 | Toronto Celtic | Tuesday May 9 – 9:00pm Ontario Soccer Centre |
| 6. | Caledon United FC Elite | 4 | vs | 1 | Prostars FC | Wednesday May 17 – 9:00pm Caledon R3 |
| 7. | Scarboro Azzurri MJ | 1 | vs | 0 | Guelph Royals PW | Tuesday May 16 – 9:00pm Ontario Soccer Centre |
| 8. | Aurora Hearts | 1 | vs | 2 | Cavan FC MJ | Thursday May 11 – 9:15pm Sheppards Bush Turf |
| 9. | Toronto Skillz | 0 | vs | 1 | Olimpia Toronto | Tuesday May 9 – 9:00pm L’Amoreaux #5 |
| 10. | GS Vets | 3 | vs | 2 | Magic AC | Wednesday May 17 – 7:00pm Ontario Soccer Centre |
| 11. | Downsview Rams | 5 | vs | 1 | Guelph Royals RW | Wednesday May 17 – 9:00pm Ontario Soccer Centre |
| 12. | GTA United | 1 | vs | 5 | Mississauga Croatia | Thursday May 11 – 7:00pm Ontario Soccer Centre |
| 13. | Panathinaikos | 2 | vs | 0 | IFC Academy | Sunday May 14 – 4:00pm St. Robs CHS |
| 14. | Burlington SC MJ | 0 | vs | 1 | Cavan FC Elite | |
| 15. | York Jets | 3 | vs | 0 | RH PARS FC | Wednesday May 10 – 7:00pm Ontario Soccer Centre |
| 16. | FC Ukraine United | 4 | vs | 0 | Georgetown Mustangs | Sunday May 7 – 9:00pm Earlscourt Park |
| 17. | Scarboro Azzurri Elite | 4 | vs | 1 | USC Karpaty | Thursday May 18 – 7:00pm Ontario Soccer Centre |
| 18. | Orangeville Athletic | 1 | vs | 4 | QPR MJ | Friday May 12 – 9:00pm Ontario Soccer Centre |
| 19. | Woodbridge Strikers | 4 | vs | 2 | Croatia Norval | Saturday May 13 – 9:00pm PFF Centre Indoor |
| 20. | AC Diavoli | 2 | vs | 3 | Scarborough Rangers | Wednesday May 24 – 9:00pm Iceland 2 |
| 21. | Bradford Wolves MJ | 1 | vs | 7 | GS United | Thursday May 18 – 9:00pm Ontario Soccer Centre |
| 22. | Queens Park Rangers | 3 | vs | 2 | CTSA Tamileelam | Thursday May 11 – 9:00pm Ontario Soccer Centre |
| 23. | Bradford Wolves RW | 2 | vs | 3 | PARS FC | Sunday May 21 – 7:00pm Crosby Park |
| 24. | Olympiakos SC | 2 | vs | 4 | Toronto Irish FC | Tuesday May 16 – 7:00pm Ontario Soccer Centre |
| 25. | Lakeshore United | 2 | vs | 1 | SC Toronto Eagles | Friday May 12 – 7:00pm Ontario Soccer Centre |
| 26. | Caledon United FC | 0 | vs | 1 | Peterborough City RE | Wednesday May 17 – 9:00pm Caledon R4 |
| 27. | Toronto Pamir | 4 | vs | 3 | Wisla United | Monday May 8 – 9:00pm Clarkson Turf |
| 28. | Markham Lightning | 1 | vs | 6 | Hrvat St. Catharines | Sunday June 4 – 3:00pm Ontario Soccer Centre |
| 29. | Burlington SC RW | 2 | vs | 5 | North York Academy | Monday May 15 – 9:00pm Ontario Soccer Centre |
| 30. | Korean Red Devils | 0 | vs | 1 | Burlington SC PW | Saturday May 13 – 7:00pm McNicoll Park |
| 31. | Vaughan Azzurri | 3 | vs | 0 | Atletico Sporting Toronto | Sunday May 14 – 9:00pm Concord Thornhill Turf |
| 32. | Peterborough City MJ | 1 | vs | 0 | Distinctionz SC | Saturday May 13 – 6:00pm Ontario Soccer Centre |
| 33. | Olympiacos Toronto | 0 | vs | 3 | Peniche CC | Monday May 15 – 7:00pm Ontario Soccer Centre |
3rd Round
| HOME | VISITOR | Game | ||||
| 34. | AIFC Men | 4 | vs | 2 | Peniche CC | Tuesday July 4 - 9:00pm The Hill Academy |
| 35. | Union FC MJ | 4 | vs | 3 | Peterborough City MJ | Wednesday June 14 - 9:00pm Henderson Field |
| 36. | Ebony Jrs | 1 | vs | 2 | Vaughan Azzurri | Saturday June 24 - 6:30pm Meadowvale (Syntex) |
| 37. | Toronto Celtic | 1 | vs | 0 | Burlington SC PW | Friday June 30 - 9:00pm Weston Lions |
| 38. | Caledon United Elite | 1 | vs | 3 | North York Academy | Monday June 5 - 9:00pm Caledon R3 |
| 39. | Scarboro Azzurri MJ | 2 | vs | 7 | Hrvat St. Catharines | Monday June 19 - 9:00pm LAmoreaux #1 |
| 40. | Cavan FC MJ | 2 | vs | 1 | Toronto Pamir | Tuesday June 27 - 8:30pm Fleming PYSC East Turf |
| 41. | Olimpia Toronto | 6 | vs | 0 | Peterborough City RE | Thursday June 29 - 9:00pm Paramount Fine Foods Centre 2 |
| 42. | GS Vets | 2 | vs | 1 | Lakeshore United | Friday June 30 - 9:00pm LAmoreaux #1 |
| 43. | Downsview Rams | 0 | vs | 4 | Toronto Irish FC | Monday July 17 - 9:00pm Esther Shiner #6 |
| 44. | Mississauga Croatia | 0 | vs | 2 | PARS FC | Thursday July 13 - 9:00pm Silver Stream Park |
| 45. | Panathinaikos | 2 | vs | 4 | Queens Park Rangers | Tuesday July 4 - 9:00pm St. Robs CHS |
| 46. | Cavan FC Elite | 1 | vs | 2 | GS United | Tuesday June 13 - 9:00pm Fleming PYSC East Turf |
| 47. | York Jets | 0 | vs | 4 | Scarborough Rangers | Thursday June 29 - 9:00pm Eglinton Flats 10 |
| 48. | FC Ukraine United | 2 | vs | 4 | Woodbridge Strikers | Monday July 3 - 8:00pm LAmoreaux #5 |
| 49. | Scarboro Azzurri Elite | 3 | vs | 1 | QPR MJ | Wednesday September 13 - 7:00pm McNicol Park |
4th Round
HOME | VISITOR | Game | ||||
| 50. | AIFC Men | vs | Scarboro Azzurri Elite | |||
| 51. | Union FC MJ | 1 | vs | 3 | Woodbridge Strikers | Monday September 11 - 9:00pm Henderson Field |
| 52. | Vaughan Azzurri | 6 | vs | 1 | Scarborough Rangers | Thursday September 14 - 9:00pm North Maple Regional Park Turf #1 |
| 53. | Toronto Celtic | vs | GS United | Tuesday September 19 - 9:00pm McNicol Park | ||
| 54. | North York Academy | 5 | vs | 2 | Queens Park Rangers | Tuesday August 1 - 9:00pm York University |
| 55. | Hrvat St. Catharines | 2 | vs | 3 | PARS FC | Tuesday August 29 - 9:00pm Heritage Green #5 |
| 56. | Cavan FC MJ | 2 | vs | 3 | Toronto Irish | Friday August 18 - 9:00pm Fleming College |
| 57. | Olimpia Toronto | vs | GS Vets | Thursday September 28 - 9:00pm Ontario Soccer Stadium |
1/4 Finals
HOME | VISITOR | Game | ||||
| 58. | Winner 50 | vs | Winner 57 | |||
| 59. | Woodbridge Strikers | vs | Toronto Irish | |||
| 60. | Vaughan Azzurri | vs | PARS FC | |||
| 61. | Winner 53 | vs | North York Academy |
Semi-Finals
HOME | VISITOR | Game | ||||
| 62. | Winner 58 | vs | Winner 61 | |||
| 63. | Winner 59 | vs | Winner 60 |
Finals
HOME | VISITOR | Game | ||||
| 64. | Winner 62 | vs | Winner 63 |
