| 32. Round | 09/02/2019 | Macclesfield Town | - | Crewe Alexandra | 3:3 | ||||
| 33. Round | 16/02/2019 | Macclesfield Town | - | Colchester United | 1:1 | ||||
| 35. Round | 02/03/2019 | Bury FC | - | Macclesfield Town | 3:0 | ||||
| 36. Round | 09/03/2019 | Macclesfield Town | - | Milton Keynes Dons | 1:3 | ||||
| 41. Round | 06/04/2019 | Macclesfield Town | - | Morecambe FC | 1:1 | ||||
| 43. Round | 19/04/2019 | Northampton Town | - | Macclesfield Town | 3:1 |
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