| 1 | Sat 9 Aug 2014 | 22-1 v Leyton OrientLeyton Orient 1-2 Chesterfield | Sky Bet League One |
| 2 | Tue 12 Aug 2014 | 23-5 v Huddersfield TownChesterfield 3-5 Huddersfield Town | Capital One Cup First Round |
| 3 | Sat 16 Aug 2014 | 22-1 v RochdaleChesterfield 2-1 Rochdale | Sky Bet League One |
| 4 | Tue 19 Aug 2014 | 20-1 v Milton Keynes DonsChesterfield 0-1 Milton Keynes Dons | Sky Bet League One |
| 5 | Sat 23 Aug 2014 | 20-0 v Fleetwood TownFleetwood Town 0-0 Chesterfield | Sky Bet League One |
| 6 | Sat 30 Aug 2014 | 22-1 v Port ValePort Vale 1-2 Chesterfield | Sky Bet League One |
| 7 | Tue 2 Sep 2014 | 20-2 v Scunthorpe UnitedScunthorpe United 2-0 Chesterfield | Johnstone's Paint Trophy Northern Area First Round |
| 8 | Sat 13 Sep 2014 | 24-1 v Scunthorpe UnitedChesterfield 4-1 Scunthorpe United | Sky Bet League One |
| 9 | Tue 16 Sep 2014 | 23-3 v Preston North EndPreston North End 3-3 Chesterfield | Sky Bet League One |
| 10 | Sat 20 Sep 2014 | 22-3 v Doncaster RoversDoncaster Rovers 3-2 Chesterfield | Sky Bet League One |
| 11 | Sat 27 Sep 2014 | 21-1 v Notts CountyChesterfield 1-1 Notts County | Sky Bet League One |
| 12 | Sat 4 Oct 2014 | 23-2 v Sheffield UnitedChesterfield 3-2 Sheffield United | Sky Bet League One |
| 13 | Sat 11 Oct 2014 | 22-3 v Bristol CityBristol City 3-2 Chesterfield | Sky Bet League One |
| 14 | Sat 18 Oct 2014 | 21-1 v Oldham AthleticChesterfield 1-1 Oldham Athletic | Sky Bet League One |
| 15 | Tue 21 Oct 2014 | 21-2 v Colchester UnitedColchester United 2-1 Chesterfield | Sky Bet League One |
| 16 | Sat 25 Oct 2014 | 20-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League One |
| 17 | Tue 28 Oct 2014 | 20-3 v Swindon TownChesterfield 0-3 Swindon Town | Sky Bet League One |
| 18 | Sat 1 Nov 2014 | 20-0 v Yeovil TownChesterfield 0-0 Yeovil Town | Sky Bet League One |
| 19 | Sun 9 Nov 2014 | 26-0 v Braintree TownBraintree Town 0-6 Chesterfield | FA Cup First Round |
| 20 | Sat 15 Nov 2014 | 20-0 v Crewe AlexandraCrewe Alexandra 0-0 Chesterfield | Sky Bet League One |
| 21 | Sat 22 Nov 2014 | 22-1 v BarnsleyChesterfield 2-1 Barnsley | Sky Bet League One |
| 22 | Sat 29 Nov 2014 | 21-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League One |
| 23 | Sat 6 Dec 2014 | 21-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Chesterfield | FA Cup Second Round |
| 24 | Sat 13 Dec 2014 | 20-1 v Bradford CityChesterfield 0-1 Bradford City | Sky Bet League One |
| 25 | Sat 20 Dec 2014 | 23-2 v GillinghamGillingham 2-3 Chesterfield | Sky Bet League One |
| 26 | Fri 26 Dec 2014 | 23-2 v Peterborough UnitedChesterfield 3-2 Peterborough United | Sky Bet League One |
| 27 | Sun 28 Dec 2014 | 20-0 v Coventry CityCoventry City 0-0 Chesterfield | Sky Bet League One |
| 28 | Fri 2 Jan 2015 | 21-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Chesterfield | FA Cup Second Round |
| 29 | Tue 6 Jan 2015 | 22-2 v Scunthorpe UnitedScunthorpe United 2-2 Chesterfield | FA Cup Third Round |
| 30 | Sat 10 Jan 2015 | 23-0 v Port ValeChesterfield 3-0 Port Vale | Sky Bet League One |
| 31 | Tue 13 Jan 2015 | 22-0 v Scunthorpe UnitedChesterfield 2-0 Scunthorpe United | FA Cup Third Round |
| 32 | Sat 17 Jan 2015 | 21-3 v Swindon TownSwindon Town 3-1 Chesterfield | Sky Bet League One |
| 33 | Sat 24 Jan 2015 | 20-2 v Derby CountyDerby County 2-0 Chesterfield | FA Cup Fourth Round |
| 34 | Tue 27 Jan 2015 | 23-0 v Crawley TownChesterfield 3-0 Crawley Town | Sky Bet League One |
| 35 | Sat 31 Jan 2015 | 22-2 v Doncaster RoversChesterfield 2-2 Doncaster Rovers | Sky Bet League One |
| 36 | Sat 7 Feb 2015 | 21-0 v Notts CountyNotts County 0-1 Chesterfield | Sky Bet League One |
| 37 | Tue 10 Feb 2015 | 20-2 v Preston North EndChesterfield 0-2 Preston North End | Sky Bet League One |
| 38 | Sat 14 Feb 2015 | 22-3 v Leyton OrientChesterfield 2-3 Leyton Orient | Sky Bet League One |
| 39 | Tue 17 Feb 2015 | 20-2 v Scunthorpe UnitedScunthorpe United 2-0 Chesterfield | Sky Bet League One |
| 40 | Sat 21 Feb 2015 | 20-1 v RochdaleRochdale 1-0 Chesterfield | Sky Bet League One |
| 41 | Sat 28 Feb 2015 | 23-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League One |
| 42 | Tue 3 Mar 2015 | 22-1 v Milton Keynes DonsMilton Keynes Dons 1-2 Chesterfield | Sky Bet League One |
| 43 | Sat 14 Mar 2015 | 22-3 v Coventry CityChesterfield 2-3 Coventry City | Sky Bet League One |
| 44 | Tue 17 Mar 2015 | 23-0 v GillinghamChesterfield 3-0 Gillingham | Sky Bet League One |
| 45 | Sat 21 Mar 2015 | 20-1 v Peterborough UnitedPeterborough United 1-0 Chesterfield | Sky Bet League One |
| 46 | Sat 28 Mar 2015 | 21-0 v WalsallChesterfield 1-0 Walsall | Sky Bet League One |
| 47 | Tue 31 Mar 2015 | 21-0 v Bradford CityBradford City 0-1 Chesterfield | Sky Bet League One |
| 48 | Fri 3 Apr 2015 | 23-2 v Yeovil TownYeovil Town 2-3 Chesterfield | Sky Bet League One |
| 49 | Mon 6 Apr 2015 | 21-0 v Crewe AlexandraChesterfield 1-0 Crewe Alexandra | Sky Bet League One |
| 50 | Sat 11 Apr 2015 | 21-1 v BarnsleyBarnsley 1-1 Chesterfield | Sky Bet League One |
| 51 | Tue 14 Apr 2015 | 26-0 v Colchester UnitedChesterfield 6-0 Colchester United | Sky Bet League One |
| 52 | Sat 18 Apr 2015 | 20-0 v Oldham AthleticOldham Athletic 0-0 Chesterfield | Sky Bet League One |
| 53 | Sat 25 Apr 2015 | 20-2 v Bristol CityChesterfield 0-2 Bristol City | Sky Bet League One |
| 54 | Sun 3 May 2015 | 21-1 v Sheffield UnitedSheffield United 1-1 Chesterfield | Sky Bet League One |
| 55 | Thu 7 May 2015 | 20-1 v Preston North EndChesterfield 0-1 Preston North End | Sky Bet League One Play-off Semi Final |
| 56 | Sun 10 May 2015 | 20-3 v Preston North EndPreston North End 3-0 Chesterfield | Sky Bet League One Play-off Semi Final |
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