13 Jun 1939 | First Round | # | Dovercourt v Riverdale | High Park, Toronto | misc922998 | |
20 Jun 1939 | Second Round | # | Broadview v Canadian National Railway | Riverdale Park, Toronto | misc923012 | |
20 Jun 1939 | Second Round | # | Toronto v Yorkshire Society | Armour Heights, Toronto | misc923013 | |
20 Jun 1939 | Second Round | # | West Toronto v Dentonia Park | High Park, Toronto | misc923014 | |
03 Jul 1939 | First Round Replay | Dovercourt v Riverdale | Toronto | misc | ||
14 Jul 1939 | Second Round | Riverdale v Grace Church | Riverdale Park, Toronto | misc | ||
18 Jul 1939 | Semi-Final | # | Yorkshire Society v Broadview | Rosedale, Toronto | misc923067 | |
25 Jul 1939 | Semi-Final | # | Dentonia Park v Grace Church | Dentonia Park, Toronto | misc923080 | |
19 Aug 1939 | Final | # | Dentonia Park v Yorkshire Society | Armour Heights, Toronto | misc923121 |
The scorecards marked with a # are potted scores only.