| 26 May 1906 | Eastern Section | Ontario Accident Insurance Company v St Barnabas | Island Park, Toronto | Results |
| 02 Jun 1906 | Eastern Section | Ontario Accident Insurance Company v Deer Park | Island Park, Toronto | Results |
| 02 Jun 1906 | Eastern Section | St Barnabas v Rosedale | St Barnabas Cricket Club Ground, Toronto | Results |
| 09 Jun 1906 | Eastern Section | St Clement's v Rosedale | Leslie Grove, Toronto | Results |
| 09 Jun 1906 | Western Section | St Cyprian's v St James' Cathedral | St Cyprian's Cricket Club Ground, Toronto | Results |
| 09 Jun 1906 | Eastern Section | Deer Park v St Barnabas | Deer Park, Toronto | Results |
| 16 Jun 1906 | Western Section | Parkdale v St James' Cathedral | Exhibition Park, Toronto | Results |
| 16 Jun 1906 | Eastern Section | Ontario Accident Insurance Company v Rosedale | Island Park, Toronto | Results |
| 16 Jun 1906 | Eastern Section | St Barnabas v St Clement's | St Barnabas Cricket Club Ground, Toronto | Results |
| 23 Jun 1906 | Eastern Section | St Clement's v Deer Park | Leslie Grove, Toronto | Results |
| 30 Jun 1906 | Western Section | St James' Cathedral v St Cyprian's | Trinity University, Toronto | Results |
| 30 Jun 1906 | Eastern Section | Deer Park v Rosedale | Deer Park, Toronto | Results |
| 07 Jul 1906 | Western Section | Dovercourt v St James' Cathedral | Dovercourt Park, Toronto | Results |
| 07 Jul 1906 | Western Section | Parkdale v St Cyprian's | Exhibition Park, Toronto | Results |
| 07 Jul 1906 | Eastern Section | Rosedale v St Clement's | Rosedale, Toronto | Results |
| 14 Jul 1906 | Eastern Section | St Clement's v St Barnabas | Leslie Grove, Toronto | Results |
| 14 Jul 1906 | Western Section | St James' Cathedral v Dovercourt | Trinity University, Toronto | Results |
| 14 Jul 1906 | Eastern Section | Deer Park v Ontario Accident Insurance Company | Deer Park, Toronto | Results |
| 21 Jul 1906 | Western Section | Dovercourt v St Cyprian's | Dovercourt Park, Toronto | Results |
| 21 Jul 1906 | Eastern Section | Rosedale v Deer Park | Rosedale, Toronto | Results |
| 28 Jul 1906 | Western Section | Dovercourt v Parkdale | Dovercourt Park, Toronto | Results |
| 28 Jul 1906 | Eastern Section | St Clement's v Ontario Accident Insurance Company | Leslie Grove, Toronto | Results |
| 28 Jul 1906 | Eastern Section | Rosedale v St Barnabas | Rosedale, Toronto | Results |
| 04 Aug 1906 | Western Section | Dovercourt v St Cyprian's | Dovercourt Park, Toronto | Results |
| 04 Aug 1906 | Eastern Section | Deer Park v St Clement's | Deer Park, Toronto | Results |
| 11 Aug 1906 | Eastern Section | Ontario Accident Insurance Company v St Clement's | Island Park, Toronto | Results |
| 11 Aug 1906 | Eastern Section | St Barnabas v Deer Park | St Barnabas Cricket Club Ground, Toronto | Results |
| 11 Aug 1906 | Western Section | St Cyprian's v Parkdale | St Cyprian's Cricket Club Ground, Toronto | Results |
| 18 Aug 1906 | Western Section | Parkdale v Dovercourt | Exhibition Park, Toronto | Results |
| 18 Aug 1906 | Eastern Section | St Barnabas v Ontario Accident Insurance Company | St Barnabas Cricket Club Ground, Toronto | Results |
| 25 Aug 1906 | Eastern Section | Rosedale v Ontario Accident Insurance Company | Rosedale, Toronto | Results |
| 25 Aug 1906 | Western Section | St James' Cathedral v Parkdale | Trinity University, Toronto | Results |
| 29 Aug 1906 | Final | Deer Park v Dovercourt | Varsity Lawn, Toronto | Results |
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