| 1. Round | 30/08/1919 | West Bromwich Albion | - | Oldham Athletic | 3:1 | ||||
| 2. Round | 01/09/1919 | Oldham Athletic | - | Manchester City | 1:3 | ||||
| 3. Round | 06/09/1919 | Oldham Athletic | - | West Bromwich Albion | 2:1 | ||||
| 6. Round | 20/09/1919 | Oldham Athletic | - | Bradford Park Avenue | 2:2 | ||||
| 14. Round | 15/11/1919 | Oldham Athletic | - | Sheffield United | 4:0 |  |
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| 15. Round | 22/11/1919 | Oldham Athletic | - | Manchester United | 0:3 | ||||
| 17. Round | 06/12/1919 | Oldham Athletic | - | Burnley FC | 1:0 | ||||
| 18. Round | 13/12/1919 | Burnley FC | - | Oldham Athletic | 2:1 | ||||
| 19. Round | 20/12/1919 | Aston Villa | - | Oldham Athletic | 3:0 | ||||
| 21. Round | 26/12/1919 | Chelsea FC | - | Oldham Athletic | 1:0 |
Wales