| 1 | Sat 25 Jan | 241-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 2 | Tue 28 Jan | 243-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 3 | Sat 1 Feb | 240-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 4 | Thu 6 Feb | 24 5-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 5 | Sat 15 Feb | 241-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 22 Feb | 240-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 7 | Sat 1 Mar | 24 1-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 8 | Tue 4 Mar | 24 0-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 8 Mar | 242-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 10 | Tue 11 Mar | 244-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 11 | Sun 11 May | 240-2 v WalsallChesterfield 0-2 Walsall | Sky Bet League Two Play-off Semi Final |
| 12 | Fri 16 May | 241-2 v WalsallWalsall 2-1 Chesterfield | Sky Bet League Two Play-off Semi Final |
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