| 1 | Wed 7 Aug 2013 | 31-2 v Leeds UnitedLeeds United 2-1 Chesterfield | Capital One Cup First Round |
| 2 | Sat 10 Aug 2013 | 32-0 v Cheltenham TownChesterfield 2-0 Cheltenham Town | Sky Bet League Two |
| 3 | Sat 17 Aug 2013 | 32-2 v RochdaleRochdale 2-2 Chesterfield | Sky Bet League Two |
| 4 | Sat 24 Aug 2013 | 32-1 v Southend UnitedChesterfield 2-1 Southend United | Sky Bet League Two |
| 5 | Sat 31 Aug 2013 | 32-0 v PortsmouthPortsmouth 0-2 Chesterfield | Sky Bet League Two |
| 6 | Sun 29 Dec 2013 | 31-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Sky Bet League Two |
| 7 | Sat 11 Jan 2014 | 34-0 v BuryChesterfield 4-0 Bury | Sky Bet League Two |
| 8 | Sat 18 Jan 2014 | 30-3 v Southend UnitedSouthend United 3-0 Chesterfield | Sky Bet League Two |
| 9 | Tue 21 Jan 2014 | 32-2 v RochdaleChesterfield 2-2 Rochdale | Sky Bet League Two |
| 10 | Sat 12 Apr 2014 | 32-1 v Hartlepool UnitedHartlepool United 1-2 Chesterfield | Sky Bet League Two |
| 11 | Fri 18 Apr 2014 | 31-1 v Exeter CityChesterfield 1-1 Exeter City | Sky Bet League Two |
| 12 | Mon 21 Apr 2014 | 31-0 v Dagenham & RedbridgeDagenham & Redbridge 0-1 Chesterfield | Sky Bet League Two |
| 13 | Sun 27 Apr 2014 | 32-0 v Burton AlbionBurton Albion 0-2 Chesterfield | Sky Bet League Two |
| 14 | Sat 3 May 2014 | 32-1 v Fleetwood TownChesterfield 2-1 Fleetwood Town | Sky Bet League Two |
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