| 1 | Sat 17 Aug | 155-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 2 | Sat 24 Aug | 151-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 3 | Tue 3 Sep | 151-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 4 | Sat 7 Dec | 153-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 5 | Tue 10 Dec | 153-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 6 | Sat 14 Dec | 152-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 21 Dec | 151-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 8 | Thu 26 Dec | 150-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 9 | Sun 29 Dec | 151-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 10 | Wed 1 Jan | 151-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 11 | Tue 14 Jan | 150-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 12 | Sat 18 Jan | 151-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 13 | Tue 4 Mar | 150-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 14 | Sat 15 Mar | 152-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
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