| 20. Round | 21/01/2020 | Macclesfield Town | - | Crewe Alexandra | 1:1 | ||||
| 29. Round | 25/01/2020 | Macclesfield Town | - | Forest Green Rovers | 2:1 | ||||
| 30. Round | 28/01/2020 | Newport County | - | Macclesfield Town | 1:0 |  |
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| 31. Round | 01/02/2020 | Macclesfield Town | - | Northampton Town | 0:1 | ||||
| 32. Round | 08/02/2020 | Leyton Orient | - | Macclesfield Town | 1:1 | ||||
| 33. Round | 11/02/2020 | Morecambe FC | - | Macclesfield Town | 2:0 | ||||
| 34. Round | 15/02/2020 | Macclesfield Town | - | Exeter City | 2:3 | ||||
| 22. Round | 18/02/2020 | Macclesfield Town | - | Plymouth Argyle | 1:1 | ||||
| 35. Round | 22/02/2020 | Crewe Alexandra | - | Macclesfield Town | 2:0 | ||||
| 37. Round | 07/03/2020 | Plymouth Argyle | - | Macclesfield Town | 3:0 |
England
