| 30 Nov 1908 | Central Section | Aura Lee v Garrett | Aura Lee Athletic Park, Toronto | Results |
| 30 Nov 1908 | Central Section | Garrett v Aura Lee | Toronto | Results |
| 30 Nov 1908 | Western Section | St Cyprian's v Weston | Exhibition Park, Toronto | Results |
| 30 Nov 1908 | Central Section | St Paul's Church v Garrett | Toronto | Results |
| 30 Nov 1908 | Western Section | West Toronto v Dovercourt | High Park, Toronto | Results |
| 30 Nov 1908 | Western Section | West Toronto v Weston | High Park, Toronto | Results |
| 24 May 1909 | Western Section | Weston v West Toronto | Weston Road Ground, Weston | Results |
| 29 May 1909 | Central Section | Grace Church v St James' Cathedral | Varsity Athletic Field, Toronto | Results |
| 29 May 1909 | Western Section | West Toronto v St Cyprian's | High Park, Toronto | Results |
| 05 Jun 1909 | Central Section | Garrett v St James' Cathedral | Toronto | Results |
| 12 Jun 1909 | Western Section | Dovercourt v Weston | not known | Results |
| 12 Jun 1909 | Central Section | St Paul's Church v St James' Cathedral | Varsity Lawn, Toronto | Results |
| 19 Jun 1909 | Central Section | Aura Lee v St James' Cathedral | Aura Lee Athletic Park, Toronto | Results |
| 19 Jun 1909 | Central Section | Garrett v Grace Church | Toronto | Results |
| 19 Jun 1909 | Western Section | Weston v St Cyprian's | Weston Road Ground, Weston | Results |
| 26 Jun 1909 | Central Section | Aura Lee v Grace Church | Aura Lee Athletic Park, Toronto | Results |
| 26 Jun 1909 | Western Section | Dovercourt v St Cyprian's | Toronto | Results |
| 26 Jun 1909 | Eastern Section | St Barnabas v Friends' Association Adult School | Toronto | Results |
| 30 Jun 1909 | Eastern Section | Friends' Association Adult School v Riverdale | Toronto | Results |
| 30 Jun 1909 | Eastern Section | St Barnabas v Riverdale | Toronto | Results |
| 10 Jul 1909 | Western Section | Dovercourt v Weston | not known | Results |
| 10 Jul 1909 | Central Section | St James' Cathedral v Garrett | Trinity University, Toronto | Results |
| 10 Jul 1909 | Central Section | St Paul's Church v Aura Lee | Varsity Lawn, Toronto | Results |
| 17 Jul 1909 | Central Section | Garrett v St Paul's Church | Toronto | Results |
| 17 Jul 1909 | Central Section | Grace Church v Aura Lee | Varsity Athletic Field, Toronto | Results |
| 17 Jul 1909 | Western Section | St Cyprian's v West Toronto | Exhibition Park, Toronto | Results |
| 24 Jul 1909 | Eastern Section | Friends' Association Adult School v St Barnabas | Centre Island Park, Toronto | Results |
| 31 Jul 1909 | Western Section | St Cyprian's v Dovercourt | Toronto | Results |
| 31 Jul 1909 | Central Section | St Paul's Church v Grace Church | Varsity Lawn, Toronto | Results |
| 07 Aug 1909 | Eastern Section | Riverdale v St Barnabas | Toronto | Results |
| 14 Aug 1909 | Central Section | Grace Church v St Paul's Church | Varsity Athletic Field, Toronto | Results |
| 14 Aug 1909 | Eastern Section | Riverdale v Friends' Association Adult School | Riverdale Park, Toronto | Results |
| 21 Aug 1909 | Central Section | Garrett v Grace Church | Aura Lee Athletic Park, Toronto | Results |
| 21 Aug 1909 | Central Section | St James' Cathedral v Aura Lee | Trinity University, Toronto | Results |
| 28 Aug 1909 | Central Section | Aura Lee v St Paul's Church | Aura Lee Athletic Park, Toronto | Results |
| 28 Aug 1909 | Western Section | Dovercourt v West Toronto | Aura Lee Athletic Park, Toronto | Results |
| 28 Aug 1909 | Central Section | St James' Cathedral v Grace Church | Trinity University, Toronto | Results |
| 04 Sep 1909 | Central Section | St Paul's Church v St James' Cathedral | Varsity Lawn, Toronto | Results |
| 11 Sep 1909 | Semi-Final | Aura Lee v West Toronto | Riverdale Park, Toronto | Results |
| 18 Sep 1909 | Final | Aura Lee v St Barnabas | Varsity Lawn, Toronto | Results |
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