| 1 | Sat 21 Feb | 101-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League Two |
| 2 | Sat 28 Feb | 100-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 3 | Tue 3 Mar | 103-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 4 | Sat 7 Mar | 102-3 v Shrewsbury TownChesterfield 2-3 Shrewsbury Town | Sky Bet League Two |
| 5 | Sat 14 Mar | 103-2 v Notts CountyNotts County 2-3 Chesterfield | Sky Bet League Two |
| 6 | Tue 17 Mar | 100-3 v Oldham AthleticChesterfield 0-3 Oldham Athletic | Sky Bet League Two |
| 7 | Sat 21 Mar | 101-0 v Accrington StanleyAccrington Stanley 0-1 Chesterfield | Sky Bet League Two |
| 8 | Fri 3 Apr | 101-0 v Cheltenham TownChesterfield 1-0 Cheltenham Town | Sky Bet League Two |
| 9 | Mon 6 Apr | 101-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 11 Apr | 101-1 v Tranmere RoversChesterfield 1-1 Tranmere Rovers | Sky Bet League Two |
| 11 | Tue 14 Apr | 102-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 12 | Sat 18 Apr | 101-1 v Fleetwood TownFleetwood Town 1-1 Chesterfield | Sky Bet League Two |
| 13 | Sat 25 Apr | 102-0 v Crewe AlexandraChesterfield 2-0 Crewe Alexandra | Sky Bet League Two |
| 14 | Sat 2 May | 10 2-1 v Swindon TownSwindon Town 1-2 Chesterfield | Sky Bet League Two |
| 15 | Sun 10 May | 100-1 v Notts CountyChesterfield 0-1 Notts County | Sky Bet League Two Play-off Semi Final |
| 16 | Fri 15 May | 100-0 v Notts CountyNotts County 0-0 Chesterfield | Sky Bet League Two Play-off Semi Final |
| 17 | Sat 8 Aug | 100-1 v Fleetwood TownFleetwood Town 1-0 Chesterfield | Carabao Cup First Round |
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