| 5. Round | 25/08/2018 | Macclesfield Town | - | Mansfield Town | 1:1 | ||||
| 6. Round | 01/09/2018 | Crewe Alexandra | - | Macclesfield Town | 3:0 | ||||
| 9. Round | 22/09/2018 | Morecambe FC | - | Macclesfield Town | 2:1 | ||||
| 19. Round | 24/11/2018 | Macclesfield Town | - | Yeovil Town | 1:0 | ||||
| 20. Round | 27/11/2018 | Exeter City | - | Macclesfield Town | 0:1 | ||||
| 29. Round | 19/01/2019 | Macclesfield Town | - | Oldham Athletic | 2:1 | ||||
| 30. Round | 26/01/2019 | Cheltenham Town | - | Macclesfield Town | 3:2 | ||||
| 31. Round | 02/02/2019 | Mansfield Town | - | Macclesfield Town | 3:1 |  |
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| 32. Round | 09/02/2019 | Macclesfield Town | - | Crewe Alexandra | 3:3 | ||||
| 36. Round | 09/03/2019 | Macclesfield Town | - | Milton Keynes Dons | 1:3 | ||||
| 38. Round | 16/03/2019 | Yeovil Town | - | Macclesfield Town | 0:2 | ||||
| 44. Round | 22/04/2019 | Macclesfield Town | - | Newport County | 0:0 | ||||
| 45. Round | 27/04/2019 | Port Vale FC | - | Macclesfield Town | 0:1 | ||||
| 46. Round | 04/05/2019 | Macclesfield Town | - | Cambridge United | 1:1 |
England