| 1 | Tue 12 Aug 2014 | 263-5 v Huddersfield TownChesterfield 3-5 Huddersfield Town | Capital One Cup First Round |
| 2 | Sat 30 Aug 2014 | 262-1 v Port ValePort Vale 1-2 Chesterfield | Sky Bet League One |
| 3 | Tue 2 Sep 2014 | 260-2 v Scunthorpe UnitedScunthorpe United 2-0 Chesterfield | Johnstone's Paint Trophy Northern Area First Round |
| 4 | Sat 13 Sep 2014 | 264-1 v Scunthorpe UnitedChesterfield 4-1 Scunthorpe United | Sky Bet League One |
| 5 | Tue 16 Sep 2014 | 263-3 v Preston North EndPreston North End 3-3 Chesterfield | Sky Bet League One |
| 6 | Sat 20 Sep 2014 | 262-3 v Doncaster RoversDoncaster Rovers 3-2 Chesterfield | Sky Bet League One |
| 7 | Sat 27 Sep 2014 | 261-1 v Notts CountyChesterfield 1-1 Notts County | Sky Bet League One |
| 8 | Sat 4 Oct 2014 | 263-2 v Sheffield UnitedChesterfield 3-2 Sheffield United | Sky Bet League One |
| 9 | Sat 11 Oct 2014 | 262-3 v Bristol CityBristol City 3-2 Chesterfield | Sky Bet League One |
| 10 | Sat 18 Oct 2014 | 261-1 v Oldham AthleticChesterfield 1-1 Oldham Athletic | Sky Bet League One |
| 11 | Tue 21 Oct 2014 | 261-2 v Colchester UnitedColchester United 2-1 Chesterfield | Sky Bet League One |
| 12 | Tue 28 Oct 2014 | 260-3 v Swindon TownChesterfield 0-3 Swindon Town | Sky Bet League One |
| 13 | Sat 1 Nov 2014 | 260-0 v Yeovil TownChesterfield 0-0 Yeovil Town | Sky Bet League One |
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