| 2. Runde | 08.10.2013 | Mansfield Town | - | Chesterfield FC | 0:1 |  |
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| Achtelfinale | 12.11.2013 | Chesterfield FC | - | Rochdale AFC | 3:0 | ||||
| Viertelfinale | 10.12.2013 | Oldham Athletic | - | Chesterfield FC | 5:6 i.E. | ||||
| Halbfinale | 04.02.2014 | Fleetwood Town | - | Chesterfield FC | 1:3 | ||||
| Halbfinale | 18.02.2014 | Chesterfield FC | - | Fleetwood Town | 0:1 | ||||
| Finale | 30.03.2014 | Chesterfield FC | - | Peterborough United | 1:3 | |
England