| 1 | Tue 2 Sep 2014 | 280-2 v Scunthorpe UnitedScunthorpe United 2-0 Chesterfield | Johnstone's Paint Trophy Northern Area First Round |
| 2 | Sat 13 Sep 2014 | 284-1 v Scunthorpe UnitedChesterfield 4-1 Scunthorpe United | Sky Bet League One |
| 3 | Tue 28 Oct 2014 | 280-3 v Swindon TownChesterfield 0-3 Swindon Town | Sky Bet League One |
| 4 | Sat 13 Dec 2014 | 280-1 v Bradford CityChesterfield 0-1 Bradford City | Sky Bet League One |
| 5 | Tue 17 Feb 2015 | 280-2 v Scunthorpe UnitedScunthorpe United 2-0 Chesterfield | Sky Bet League One |
| 6 | Sat 21 Feb 2015 | 280-1 v RochdaleRochdale 1-0 Chesterfield | Sky Bet League One |
| 7 | Sat 28 Feb 2015 | 283-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League One |
| 8 | Tue 3 Mar 2015 | 282-1 v Milton Keynes DonsMilton Keynes Dons 1-2 Chesterfield | Sky Bet League One |
| 9 | Sat 14 Mar 2015 | 282-3 v Coventry CityChesterfield 2-3 Coventry City | Sky Bet League One |
| 10 | Tue 17 Mar 2015 | 283-0 v GillinghamChesterfield 3-0 Gillingham | Sky Bet League One |
| 11 | Sat 21 Mar 2015 | 280-1 v Peterborough UnitedPeterborough United 1-0 Chesterfield | Sky Bet League One |
| 12 | Sat 28 Mar 2015 | 281-0 v WalsallChesterfield 1-0 Walsall | Sky Bet League One |
| 13 | Fri 3 Apr 2015 | 283-2 v Yeovil TownYeovil Town 2-3 Chesterfield | Sky Bet League One |
| 14 | Mon 6 Apr 2015 | 281-0 v Crewe AlexandraChesterfield 1-0 Crewe Alexandra | Sky Bet League One |
| 15 | Sat 11 Apr 2015 | 281-1 v BarnsleyBarnsley 1-1 Chesterfield | Sky Bet League One |
| 16 | Tue 14 Apr 2015 | 286-0 v Colchester UnitedChesterfield 6-0 Colchester United | Sky Bet League One |
| 17 | Sat 25 Apr 2015 | 280-2 v Bristol CityChesterfield 0-2 Bristol City | Sky Bet League One |
| 18 | Sun 3 May 2015 | 281-1 v Sheffield UnitedSheffield United 1-1 Chesterfield | Sky Bet League One |
| 19 | Sun 10 May 2015 | 280-3 v Preston North EndPreston North End 3-0 Chesterfield | Sky Bet League One Play-off Semi Final |
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