| 1 | Sat 11 Jan 2014 | 264-0 v BuryChesterfield 4-0 Bury | Sky Bet League Two |
| 2 | Sat 18 Jan 2014 | 260-3 v Southend UnitedSouthend United 3-0 Chesterfield | Sky Bet League Two |
| 3 | Sat 25 Jan 2014 | 263-1 v Northampton TownNorthampton Town 1-3 Chesterfield | Sky Bet League Two |
| 4 | Tue 28 Jan 2014 | 262-0 v York CityYork City 0-2 Chesterfield | Sky Bet League Two |
| 5 | Sat 1 Feb 2014 | 263-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 6 | Tue 4 Feb 2014 | 263-1 v Fleetwood TownFleetwood Town 1-3 Chesterfield | Johnstone's Paint Trophy Northern Area Final |
| 7 | Sat 8 Feb 2014 | 261-1 v Scunthorpe UnitedScunthorpe United 1-1 Chesterfield | Sky Bet League Two |
| 8 | Sat 15 Feb 2014 | 263-1 v Torquay UnitedChesterfield 3-1 Torquay United | Sky Bet League Two |
| 9 | Sat 22 Feb 2014 | 260-1 v Wycombe WanderersWycombe Wanderers 1-0 Chesterfield | Sky Bet League Two |
| 10 | Tue 25 Feb 2014 | 264-1 v Cheltenham TownCheltenham Town 1-4 Chesterfield | Sky Bet League Two |
| 11 | Mon 3 Mar 2014 | 260-0 v PortsmouthChesterfield 0-0 Portsmouth | Sky Bet League Two |
| 12 | Sat 8 Mar 2014 | 261-3 v Accrington StanleyAccrington Stanley 3-1 Chesterfield | Sky Bet League Two |
| 13 | Sat 12 Apr 2014 | 262-1 v Hartlepool UnitedHartlepool United 1-2 Chesterfield | Sky Bet League Two |
| 14 | Fri 18 Apr 2014 | 261-1 v Exeter CityChesterfield 1-1 Exeter City | Sky Bet League Two |
| 15 | Mon 21 Apr 2014 | 261-0 v Dagenham & RedbridgeDagenham & Redbridge 0-1 Chesterfield | Sky Bet League Two |
| 16 | Sun 27 Apr 2014 | 262-0 v Burton AlbionBurton Albion 0-2 Chesterfield | Sky Bet League Two |
| 17 | Sat 3 May 2014 | 262-1 v Fleetwood TownChesterfield 2-1 Fleetwood Town | Sky Bet League Two |
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