| 1 | Tue 8 Oct 2013 | 21-0 v Mansfield TownMansfield Town 0-1 Chesterfield | Johnstone's Paint Trophy Northern Area Second Round |
| 2 | Sat 26 Oct 2013 | 20-0 v Bristol RoversBristol Rovers 0-0 Chesterfield | Sky Bet League Two |
| 3 | Sat 2 Nov 2013 | 21-1 v Scunthorpe UnitedChesterfield 1-1 Scunthorpe United | Sky Bet League Two |
| 4 | Sat 9 Nov 2013 | 22-0 v Daventry TownChesterfield 2-0 Daventry Town | FA Cup with Budweiser First Round |
| 5 | Tue 12 Nov 2013 | 23-0 v RochdaleChesterfield 3-0 Rochdale | Johnstone's Paint Trophy Northern Area Quarter Final |
| 6 | Sat 16 Nov 2013 | 22-0 v Torquay UnitedTorquay United 0-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 23 Nov 2013 | 22-0 v Wycombe WanderersChesterfield 2-0 Wycombe Wanderers | Sky Bet League Two |
| 8 | Tue 26 Nov 2013 | 20-0 v Northampton TownChesterfield 0-0 Northampton Town | Sky Bet League Two |
| 9 | Sun 1 Dec 2013 | 22-3 v Newport CountyNewport County 3-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 7 Dec 2013 | 21-3 v Southend UnitedChesterfield 1-3 Southend United | FA Cup with Budweiser Second Round |
| 11 | Tue 10 Dec 2013 | 21-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Johnstone's Paint Trophy Northern Area Semi Final |
| 12 | Fri 20 Dec 2013 | 22-0 v Exeter CityExeter City 0-2 Chesterfield | Sky Bet League Two |
| 13 | Thu 26 Dec 2013 | 21-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | Sky Bet League Two |
| 14 | Sun 29 Dec 2013 | 21-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Sky Bet League Two |
| 15 | Sat 11 Jan 2014 | 24-0 v BuryChesterfield 4-0 Bury | Sky Bet League Two |
| 16 | Sat 18 Jan 2014 | 20-3 v Southend UnitedSouthend United 3-0 Chesterfield | Sky Bet League Two |
| 17 | Tue 21 Jan 2014 | 22-2 v RochdaleChesterfield 2-2 Rochdale | Sky Bet League Two |
| 18 | Sat 25 Jan 2014 | 23-1 v Northampton TownNorthampton Town 1-3 Chesterfield | Sky Bet League Two |
| 19 | Tue 28 Jan 2014 | 22-0 v York CityYork City 0-2 Chesterfield | Sky Bet League Two |
| 20 | Sat 1 Feb 2014 | 23-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 21 | Tue 4 Feb 2014 | 23-1 v Fleetwood TownFleetwood Town 1-3 Chesterfield | Johnstone's Paint Trophy Northern Area Final |
| 22 | Sat 8 Feb 2014 | 21-1 v Scunthorpe UnitedScunthorpe United 1-1 Chesterfield | Sky Bet League Two |
| 23 | Sat 15 Feb 2014 | 23-1 v Torquay UnitedChesterfield 3-1 Torquay United | Sky Bet League Two |
| 24 | Tue 25 Feb 2014 | 24-1 v Cheltenham TownCheltenham Town 1-4 Chesterfield | Sky Bet League Two |
| 25 | Mon 3 Mar 2014 | 20-0 v PortsmouthChesterfield 0-0 Portsmouth | Sky Bet League Two |
| 26 | Sat 8 Mar 2014 | 21-3 v Accrington StanleyAccrington Stanley 3-1 Chesterfield | Sky Bet League Two |
| 27 | Tue 11 Mar 2014 | 21-1 v AFC WimbledonAFC Wimbledon 1-1 Chesterfield | Sky Bet League Two |
| 28 | Sat 15 Mar 2014 | 23-0 v Oxford UnitedChesterfield 3-0 Oxford United | Sky Bet League Two |
| 29 | Tue 18 Mar 2014 | 21-2 v Plymouth ArgylePlymouth Argyle 2-1 Chesterfield | Sky Bet League Two |
| 30 | Sat 22 Mar 2014 | 20-0 v Mansfield TownMansfield Town 0-0 Chesterfield | Sky Bet League Two |
| 31 | Tue 25 Mar 2014 | 21-0 v MorecambeChesterfield 1-0 Morecambe | Sky Bet League Two |
| 32 | Sun 30 Mar 2014 | 21-3 v Peterborough UnitedChesterfield 1-3 Peterborough United | Johnstone's Paint Trophy Final |
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