| 1. Round | 04/08/2018 | Oldham Athletic | - | Milton Keynes Dons | 1:2 | ||||
| 3. Round | 18/08/2018 | Oldham Athletic | - | Macclesfield Town | 3:1 |  |
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| 6. Round | 01/09/2018 | Oldham Athletic | - | Crawley Town | 2:1 | |
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| 7. Round | 08/09/2018 | Oldham Athletic | - | Newport County | 0:1 | ||||
| 8. Round | 15/09/2018 | Grimsby Town | - | Oldham Athletic | 0:3 | |
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| 9. Round | 22/09/2018 | Oldham Athletic | - | Colchester United | 3:3 | |
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| 12. Round | 06/10/2018 | Oldham Athletic | - | Carlisle United | 1:3 | ||||
| 18. Round | 17/11/2018 | Oldham Athletic | - | Cambridge United | 3:1 | ||||
| 19. Round | 24/11/2018 | Tranmere Rovers | - | Oldham Athletic | 1:1 | ||||
| 20. Round | 27/11/2018 | Oldham Athletic | - | Lincoln City | 1:1 |  |
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| 21. Round | 08/12/2018 | Crewe Alexandra | - | Oldham Athletic | 0:2 | |
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| 22. Round | 15/12/2018 | Oldham Athletic | - | Bury FC | 4:2 | |
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| 23. Round | 22/12/2018 | Oldham Athletic | - | Exeter City | 2:3 | |
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| 24. Round | 26/12/2018 | Carlisle United | - | Oldham Athletic | 6:0 | ||||
| 26. Round | 01/01/2019 | Oldham Athletic | - | Notts County | 2:0 |
England