| 1 | Sat 3 Aug 2013 | 12-0 v BuryBury 0-2 Chesterfield | Sky Bet League Two |
| 2 | Wed 7 Aug 2013 | 11-2 v Leeds UnitedLeeds United 2-1 Chesterfield | Capital One Cup First Round |
| 3 | Sat 10 Aug 2013 | 12-0 v Cheltenham TownChesterfield 2-0 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 17 Aug 2013 | 12-2 v RochdaleRochdale 2-2 Chesterfield | Sky Bet League Two |
| 5 | Sat 24 Aug 2013 | 12-1 v Southend UnitedChesterfield 2-1 Southend United | Sky Bet League Two |
| 6 | Sat 31 Aug 2013 | 12-0 v PortsmouthPortsmouth 0-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 7 Sep 2013 | 11-0 v Accrington StanleyChesterfield 1-0 Accrington Stanley | Sky Bet League Two |
| 8 | Sat 14 Sep 2013 | 12-0 v AFC WimbledonChesterfield 2-0 AFC Wimbledon | Sky Bet League Two |
| 9 | Sat 21 Sep 2013 | 11-0 v Oxford UnitedOxford United 0-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 28 Sep 2013 | 10-1 v Mansfield TownChesterfield 0-1 Mansfield Town | Sky Bet League Two |
| 11 | Sat 5 Oct 2013 | 13-4 v MorecambeMorecambe 4-3 Chesterfield | Sky Bet League Two |
| 12 | Tue 8 Oct 2013 | 11-0 v Mansfield TownMansfield Town 0-1 Chesterfield | Johnstone's Paint Trophy Northern Area Second Round |
| 13 | Sat 12 Oct 2013 | 11-1 v Fleetwood TownFleetwood Town 1-1 Chesterfield | Sky Bet League Two |
| 14 | Sat 19 Oct 2013 | 10-2 v Burton AlbionChesterfield 0-2 Burton Albion | Sky Bet League Two |
| 15 | Tue 22 Oct 2013 | 12-2 v York CityChesterfield 2-2 York City | Sky Bet League Two |
| 16 | Sat 26 Oct 2013 | 10-0 v Bristol RoversBristol Rovers 0-0 Chesterfield | Sky Bet League Two |
| 17 | Sat 2 Nov 2013 | 11-1 v Scunthorpe UnitedChesterfield 1-1 Scunthorpe United | Sky Bet League Two |
| 18 | Sat 9 Nov 2013 | 12-0 v Daventry TownChesterfield 2-0 Daventry Town | FA Cup with Budweiser First Round |
| 19 | Tue 12 Nov 2013 | 13-0 v RochdaleChesterfield 3-0 Rochdale | Johnstone's Paint Trophy Northern Area Quarter Final |
| 20 | Sat 16 Nov 2013 | 12-0 v Torquay UnitedTorquay United 0-2 Chesterfield | Sky Bet League Two |
| 21 | Sat 23 Nov 2013 | 12-0 v Wycombe WanderersChesterfield 2-0 Wycombe Wanderers | Sky Bet League Two |
| 22 | Tue 26 Nov 2013 | 10-0 v Northampton TownChesterfield 0-0 Northampton Town | Sky Bet League Two |
| 23 | Sun 1 Dec 2013 | 12-3 v Newport CountyNewport County 3-2 Chesterfield | Sky Bet League Two |
| 24 | Sat 7 Dec 2013 | 11-3 v Southend UnitedChesterfield 1-3 Southend United | FA Cup with Budweiser Second Round |
| 25 | Tue 10 Dec 2013 | 11-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Johnstone's Paint Trophy Northern Area Semi Final |
| 26 | Sat 14 Dec 2013 | 12-0 v Plymouth ArgyleChesterfield 2-0 Plymouth Argyle | Sky Bet League Two |
| 27 | Fri 20 Dec 2013 | 12-0 v Exeter CityExeter City 0-2 Chesterfield | Sky Bet League Two |
| 28 | Thu 26 Dec 2013 | 11-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | Sky Bet League Two |
| 29 | Sun 29 Dec 2013 | 11-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Sky Bet League Two |
| 30 | Sat 11 Jan 2014 | 14-0 v BuryChesterfield 4-0 Bury | Sky Bet League Two |
| 31 | Sat 18 Jan 2014 | 10-3 v Southend UnitedSouthend United 3-0 Chesterfield | Sky Bet League Two |
| 32 | Tue 21 Jan 2014 | 12-2 v RochdaleChesterfield 2-2 Rochdale | Sky Bet League Two |
| 33 | Sat 25 Jan 2014 | 13-1 v Northampton TownNorthampton Town 1-3 Chesterfield | Sky Bet League Two |
| 34 | Tue 28 Jan 2014 | 12-0 v York CityYork City 0-2 Chesterfield | Sky Bet League Two |
| 35 | Sat 1 Feb 2014 | 13-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 36 | Tue 4 Feb 2014 | 13-1 v Fleetwood TownFleetwood Town 1-3 Chesterfield | Johnstone's Paint Trophy Northern Area Final |
| 37 | Sat 8 Feb 2014 | 11-1 v Scunthorpe UnitedScunthorpe United 1-1 Chesterfield | Sky Bet League Two |
| 38 | Sat 15 Feb 2014 | 13-1 v Torquay UnitedChesterfield 3-1 Torquay United | Sky Bet League Two |
| 39 | Tue 18 Feb 2014 | 10-1 v Fleetwood TownChesterfield 0-1 Fleetwood Town | Johnstone's Paint Trophy Northern Area Final |
| 40 | Sat 22 Feb 2014 | 10-1 v Wycombe WanderersWycombe Wanderers 1-0 Chesterfield | Sky Bet League Two |
| 41 | Tue 25 Feb 2014 | 14-1 v Cheltenham TownCheltenham Town 1-4 Chesterfield | Sky Bet League Two |
| 42 | Mon 3 Mar 2014 | 10-0 v PortsmouthChesterfield 0-0 Portsmouth | Sky Bet League Two |
| 43 | Sat 8 Mar 2014 | 11-3 v Accrington StanleyAccrington Stanley 3-1 Chesterfield | Sky Bet League Two |
| 44 | Tue 11 Mar 2014 | 11-1 v AFC WimbledonAFC Wimbledon 1-1 Chesterfield | Sky Bet League Two |
| 45 | Sat 15 Mar 2014 | 13-0 v Oxford UnitedChesterfield 3-0 Oxford United | Sky Bet League Two |
| 46 | Tue 18 Mar 2014 | 11-2 v Plymouth ArgylePlymouth Argyle 2-1 Chesterfield | Sky Bet League Two |
| 47 | Sat 22 Mar 2014 | 10-0 v Mansfield TownMansfield Town 0-0 Chesterfield | Sky Bet League Two |
| 48 | Tue 25 Mar 2014 | 11-0 v MorecambeChesterfield 1-0 Morecambe | Sky Bet League Two |
| 49 | Sun 30 Mar 2014 | 11-3 v Peterborough UnitedChesterfield 1-3 Peterborough United | Johnstone's Paint Trophy Final |
| 50 | Sat 5 Apr 2014 | 11-1 v Newport CountyChesterfield 1-1 Newport County | Sky Bet League Two |
| 51 | Sat 12 Apr 2014 | 12-1 v Hartlepool UnitedHartlepool United 1-2 Chesterfield | Sky Bet League Two |
| 52 | Fri 18 Apr 2014 | 11-1 v Exeter CityChesterfield 1-1 Exeter City | Sky Bet League Two |
| 53 | Mon 21 Apr 2014 | 11-0 v Dagenham & RedbridgeDagenham & Redbridge 0-1 Chesterfield | Sky Bet League Two |
| 54 | Sun 27 Apr 2014 | 12-0 v Burton AlbionBurton Albion 0-2 Chesterfield | Sky Bet League Two |
| 55 | Sat 3 May 2014 | 12-1 v Fleetwood TownChesterfield 2-1 Fleetwood Town | Sky Bet League Two |
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