| 1 | Tue 7 Oct | 441-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 2 | Sat 18 Oct | 441-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 3 | Sat 1 Nov | 441-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 4 | Sat 8 Nov | 443-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 5 | Tue 11 Nov | 442-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 6 | Sat 15 Nov | 441-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 7 | Sat 22 Nov | 443-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 8 | Mon 29 Dec | 440-1 v Cambridge UnitedChesterfield 0-1 Cambridge United | Sky Bet League Two |
| 9 | Thu 1 Jan | 441-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 10 | Sun 4 Jan | 442-2 v Milton Keynes DonsMilton Keynes Dons 2-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 7 Feb | 443-2 v Bristol RoversBristol Rovers 2-3 Chesterfield | Sky Bet League Two |
| 12 | Sat 14 Feb | 441-1 v Harrogate TownChesterfield 1-1 Harrogate Town | Sky Bet League Two |
| 13 | Sat 28 Feb | 440-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 14 | Tue 3 Mar | 44 3-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 15 | Sat 14 Mar | 443-2 v Notts CountyNotts County 2-3 Chesterfield | Sky Bet League Two |
| 16 | Sat 21 Mar | 441-0 v Accrington StanleyAccrington Stanley 0-1 Chesterfield | Sky Bet League Two |
| 17 | Fri 3 Apr | 441-0 v Cheltenham TownChesterfield 1-0 Cheltenham Town | Sky Bet League Two |
| 18 | Mon 6 Apr | 441-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 19 | Sat 11 Apr | 441-1 v Tranmere RoversChesterfield 1-1 Tranmere Rovers | Sky Bet League Two |
| 20 | Tue 14 Apr | 442-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 21 | Sat 18 Apr | 441-1 v Fleetwood TownFleetwood Town 1-1 Chesterfield | Sky Bet League Two |
| 22 | Sat 25 Apr | 442-0 v Crewe AlexandraChesterfield 2-0 Crewe Alexandra | Sky Bet League Two |
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