| 31. Jornada | 18.01.2020 | Eastleigh FC | - | Chesterfield FC | 0:2 | ||||
| 32. Jornada | 25.01.2020 | Chesterfield FC | - | AFC Fylde | 1:1 | ||||
| 33. Jornada | 01.02.2020 | Notts County | - | Chesterfield FC | 3:0 | ||||
| 34. Jornada | 08.02.2020 | Chesterfield FC | - | Wrexham AFC | 3:2 | ||||
| 36. Jornada | 22.02.2020 | Chesterfield FC | - | Ebbsfleet United | 4:0 | ||||
| 37. Jornada | 03.03.2020 | Chesterfield FC | - | Harrogate Town | 3:4 | ||||
| 38. Jornada | 07.03.2020 | Chorley FC | - | Chesterfield FC | 1:2 |  |
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| 39. Jornada | 14.03.2020 | Dover Athletic | - | Chesterfield FC | 1:1 |
Inglaterra