| 1. Round | 30/08/1919 | West Bromwich Albion | - | Oldham Athletic | 3:1 | ||||
| 2. Round | 01/09/1919 | Oldham Athletic | - | Manchester City | 1:3 |  |
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| 3. Round | 06/09/1919 | Oldham Athletic | - | West Bromwich Albion | 2:1 | |
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| 4. Round | 08/09/1919 | Manchester City | - | Oldham Athletic | 3:1 | ||||
| 5. Round | 13/09/1919 | Bradford Park Avenue | - | Oldham Athletic | 2:0 | ||||
| 7. Round | 27/09/1919 | Preston North End | - | Oldham Athletic | 2:1 | |
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| 8. Round | 04/10/1919 | Oldham Athletic | - | Preston North End | 4:1 | |
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| 9. Round | 11/10/1919 | Middlesbrough FC | - | Oldham Athletic | 1:0 | ||||
| 11. Round | 25/10/1919 | Derby County | - | Oldham Athletic | 1:1 | ||||
| 12. Round | 01/11/1919 | Oldham Athletic | - | Derby County | 3:0 | ||||
| 13. Round | 08/11/1919 | Sheffield United | - | Oldham Athletic | 1:0 | ||||
| 22. Round | 27/12/1919 | Oldham Athletic | - | Aston Villa | 0:3 | ||||
| 20. Round | 01/01/1920 | Oldham Athletic | - | Chelsea FC | 1:0 | ||||
| 23. Round | 03/01/1920 | Newcastle United | - | Oldham Athletic | 0:1 | ||||
| 40. Round | 24/04/1920 | Notts County | - | Oldham Athletic | 2:1 |
England