| 1 | Sat 6 Aug 2016 | 21-1 v Oxford UnitedOxford United 1-1 Chesterfield | Sky Bet League One |
| 2 | Tue 9 Aug 2016 | 21-3 v RochdaleRochdale 3-1 Chesterfield | EFL Cup First Round |
| 3 | Sat 13 Aug 2016 | 23-1 v Swindon TownChesterfield 3-1 Swindon Town | Sky Bet League One |
| 4 | Tue 16 Aug 2016 | 22-0 v WalsallChesterfield 2-0 Walsall | Sky Bet League One |
| 5 | Sat 20 Aug 2016 | 21-2 v Shrewsbury TownShrewsbury Town 2-1 Chesterfield | Sky Bet League One |
| 6 | Sat 27 Aug 2016 | 21-3 v MillwallChesterfield 1-3 Millwall | Sky Bet League One |
| 7 | Sat 3 Sep 2016 | 21-2 v AFC WimbledonAFC Wimbledon 2-1 Chesterfield | Sky Bet League One |
| 8 | Sat 10 Sep 2016 | 20-0 v Oldham AthleticOldham Athletic 0-0 Chesterfield | Sky Bet League One |
| 9 | Sat 17 Sep 2016 | 23-1 v Northampton TownChesterfield 3-1 Northampton Town | Sky Bet League One |
| 10 | Sat 24 Sep 2016 | 21-2 v BuryBury 2-1 Chesterfield | Sky Bet League One |
| 11 | Tue 18 Oct 2016 | 20-1 v Fleetwood TownChesterfield 0-1 Fleetwood Town | Sky Bet League One |
| 12 | Sat 18 Mar 2017 | 21-2 v Bristol RoversBristol Rovers 2-1 Chesterfield | Sky Bet League One |
| 13 | Sat 25 Mar 2017 | 21-3 v RochdaleChesterfield 1-3 Rochdale | Sky Bet League One |
| 14 | Sat 1 Apr 2017 | 20-0 v Bolton WanderersBolton Wanderers 0-0 Chesterfield | Sky Bet League One |
| 15 | Sat 8 Apr 2017 | 21-0 v Port ValeChesterfield 1-0 Port Vale | Sky Bet League One |
| 16 | Fri 14 Apr 2017 | 20-4 v Southend UnitedChesterfield 0-4 Southend United | Sky Bet League One |
| 17 | Mon 17 Apr 2017 | 21-3 v Scunthorpe UnitedScunthorpe United 3-1 Chesterfield | Sky Bet League One |
| 18 | Sat 22 Apr 2017 | 21-2 v Charlton AthleticChesterfield 1-2 Charlton Athletic | Sky Bet League One |
| 19 | Sun 30 Apr 2017 | 22-3 v Sheffield UnitedSheffield United 3-2 Chesterfield | Sky Bet League One |
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