| 1 | Sat 3 Aug 2013 | 52-0 v BuryBury 0-2 Chesterfield | Sky Bet League Two |
| 2 | Wed 7 Aug 2013 | 51-2 v Leeds UnitedLeeds United 2-1 Chesterfield | Capital One Cup First Round |
| 3 | Sat 10 Aug 2013 | 52-0 v Cheltenham TownChesterfield 2-0 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 17 Aug 2013 | 52-2 v RochdaleRochdale 2-2 Chesterfield | Sky Bet League Two |
| 5 | Sat 24 Aug 2013 | 52-1 v Southend UnitedChesterfield 2-1 Southend United | Sky Bet League Two |
| 6 | Sat 31 Aug 2013 | 52-0 v PortsmouthPortsmouth 0-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 7 Sep 2013 | 51-0 v Accrington StanleyChesterfield 1-0 Accrington Stanley | Sky Bet League Two |
| 8 | Sat 14 Sep 2013 | 52-0 v AFC WimbledonChesterfield 2-0 AFC Wimbledon | Sky Bet League Two |
| 9 | Sat 21 Sep 2013 | 51-0 v Oxford UnitedOxford United 0-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 28 Sep 2013 | 50-1 v Mansfield TownChesterfield 0-1 Mansfield Town | Sky Bet League Two |
| 11 | Sat 5 Oct 2013 | 53-4 v MorecambeMorecambe 4-3 Chesterfield | Sky Bet League Two |
| 12 | Tue 8 Oct 2013 | 161-0 v Mansfield TownMansfield Town 0-1 Chesterfield | Johnstone's Paint Trophy Northern Area Second Round |
| 13 | Sat 12 Oct 2013 | 51-1 v Fleetwood TownFleetwood Town 1-1 Chesterfield | Sky Bet League Two |
| 14 | Sat 19 Oct 2013 | 50-2 v Burton AlbionChesterfield 0-2 Burton Albion | Sky Bet League Two |
| 15 | Tue 22 Oct 2013 | 52-2 v York CityChesterfield 2-2 York City | Sky Bet League Two |
| 16 | Sat 26 Oct 2013 | 50-0 v Bristol RoversBristol Rovers 0-0 Chesterfield | Sky Bet League Two |
| 17 | Fri 20 Dec 2013 | 52-0 v Exeter CityExeter City 0-2 Chesterfield | Sky Bet League Two |
| 18 | Sat 11 Jan 2014 | 54-0 v BuryChesterfield 4-0 Bury | Sky Bet League Two |
| 19 | Sat 18 Jan 2014 | 50-3 v Southend UnitedSouthend United 3-0 Chesterfield | Sky Bet League Two |
| 20 | Tue 21 Jan 2014 | 52-2 v RochdaleChesterfield 2-2 Rochdale | Sky Bet League Two |
| 21 | Sat 25 Jan 2014 | 53-1 v Northampton TownNorthampton Town 1-3 Chesterfield | Sky Bet League Two |
| 22 | Tue 28 Jan 2014 | 52-0 v York CityYork City 0-2 Chesterfield | Sky Bet League Two |
| 23 | Sat 1 Feb 2014 | 53-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 24 | Tue 4 Feb 2014 | 53-1 v Fleetwood TownFleetwood Town 1-3 Chesterfield | Johnstone's Paint Trophy Northern Area Final |
| 25 | Sat 8 Feb 2014 | 51-1 v Scunthorpe UnitedScunthorpe United 1-1 Chesterfield | Sky Bet League Two |
| 26 | Sat 15 Feb 2014 | 53-1 v Torquay UnitedChesterfield 3-1 Torquay United | Sky Bet League Two |
| 27 | Tue 18 Feb 2014 | 50-1 v Fleetwood TownChesterfield 0-1 Fleetwood Town | Johnstone's Paint Trophy Northern Area Final |
| 28 | Sat 22 Feb 2014 | 50-1 v Wycombe WanderersWycombe Wanderers 1-0 Chesterfield | Sky Bet League Two |
| 29 | Tue 25 Feb 2014 | 54-1 v Cheltenham TownCheltenham Town 1-4 Chesterfield | Sky Bet League Two |
| 30 | Mon 3 Mar 2014 | 50-0 v PortsmouthChesterfield 0-0 Portsmouth | Sky Bet League Two |
| 31 | Sat 8 Mar 2014 | 51-3 v Accrington StanleyAccrington Stanley 3-1 Chesterfield | Sky Bet League Two |
| 32 | Tue 11 Mar 2014 | 51-1 v AFC WimbledonAFC Wimbledon 1-1 Chesterfield | Sky Bet League Two |
| 33 | Sat 15 Mar 2014 | 53-0 v Oxford UnitedChesterfield 3-0 Oxford United | Sky Bet League Two |
| 34 | Tue 18 Mar 2014 | 51-2 v Plymouth ArgylePlymouth Argyle 2-1 Chesterfield | Sky Bet League Two |
| 35 | Sat 22 Mar 2014 | 50-0 v Mansfield TownMansfield Town 0-0 Chesterfield | Sky Bet League Two |
| 36 | Tue 25 Mar 2014 | 51-0 v MorecambeChesterfield 1-0 Morecambe | Sky Bet League Two |
| 37 | Sun 30 Mar 2014 | 51-3 v Peterborough UnitedChesterfield 1-3 Peterborough United | Johnstone's Paint Trophy Final |
| 38 | Sat 5 Apr 2014 | 51-1 v Newport CountyChesterfield 1-1 Newport County | Sky Bet League Two |
| 39 | Sat 12 Apr 2014 | 52-1 v Hartlepool UnitedHartlepool United 1-2 Chesterfield | Sky Bet League Two |
| 40 | Fri 18 Apr 2014 | 51-1 v Exeter CityChesterfield 1-1 Exeter City | Sky Bet League Two |
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