| 17. Round | 02/11/2019 | Carlisle United | - | Macclesfield Town | 2:1 | ||||
| 18. Round | 16/11/2019 | Macclesfield Town | - | Mansfield Town | 0:0 | ||||
| 19. Round | 23/11/2019 | Salford City | - | Macclesfield Town | 0:0 | ||||
| 16. Round | 30/11/2019 | Macclesfield Town | - | Bradford City | 1:1 | ||||
| 21. Round | 14/12/2019 | Walsall FC | - | Macclesfield Town | 1:1 | ||||
| 23. Round | 26/12/2019 | Macclesfield Town | - | Grimsby Town | 1:1 | ||||
| 24. Round | 29/12/2019 | Forest Green Rovers | - | Macclesfield Town | 1:0 | ||||
| 26. Round | 04/01/2020 | Macclesfield Town | - | Cambridge United | 1:0 | ||||
| 27. Round | 11/01/2020 | Macclesfield Town | - | Oldham Athletic | 1:1 | ||||
| 28. Round | 18/01/2020 | Colchester United | - | Macclesfield Town | 2:1 | ||||
| 20. Round | 21/01/2020 | Macclesfield Town | - | Crewe Alexandra | 1:1 | ||||
| 31. Round | 01/02/2020 | Macclesfield Town | - | Northampton Town | 0:1 | ||||
| 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 | ||||
| 36. Round | 29/02/2020 | Macclesfield Town | - | Salford City | 0:2 |
England