| 1 | Sat 6 Aug 2016 | 51-1 v Oxford UnitedOxford United 1-1 Chesterfield | Sky Bet League One |
| 2 | Tue 9 Aug 2016 | 51-3 v RochdaleRochdale 3-1 Chesterfield | EFL Cup First Round |
| 3 | Sat 13 Aug 2016 | 53-1 v Swindon TownChesterfield 3-1 Swindon Town | Sky Bet League One |
| 4 | Tue 16 Aug 2016 | 52-0 v WalsallChesterfield 2-0 Walsall | Sky Bet League One |
| 5 | Sat 20 Aug 2016 | 51-2 v Shrewsbury TownShrewsbury Town 2-1 Chesterfield | Sky Bet League One |
| 6 | Sat 27 Aug 2016 | 51-3 v MillwallChesterfield 1-3 Millwall | Sky Bet League One |
| 7 | Sat 3 Sep 2016 | 51-2 v AFC WimbledonAFC Wimbledon 2-1 Chesterfield | Sky Bet League One |
| 8 | Sat 10 Sep 2016 | 50-0 v Oldham AthleticOldham Athletic 0-0 Chesterfield | Sky Bet League One |
| 9 | Sat 17 Sep 2016 | 53-1 v Northampton TownChesterfield 3-1 Northampton Town | Sky Bet League One |
| 10 | Sat 24 Sep 2016 | 51-2 v BuryBury 2-1 Chesterfield | Sky Bet League One |
| 11 | Tue 27 Sep 2016 | 53-3 v GillinghamChesterfield 3-3 Gillingham | Sky Bet League One |
| 12 | Sat 1 Oct 2016 | 50-1 v Bradford CityChesterfield 0-1 Bradford City | Sky Bet League One |
| 13 | Sat 15 Oct 2016 | 50-1 v Southend UnitedSouthend United 1-0 Chesterfield | Sky Bet League One |
| 14 | Tue 18 Oct 2016 | 50-1 v Fleetwood TownChesterfield 0-1 Fleetwood Town | Sky Bet League One |
| 15 | Sat 22 Oct 2016 | 50-3 v Scunthorpe UnitedChesterfield 0-3 Scunthorpe United | Sky Bet League One |
| 16 | Sat 29 Oct 2016 | 50-1 v Charlton AthleticCharlton Athletic 1-0 Chesterfield | Sky Bet League One |
| 17 | Tue 1 Nov 2016 | 50-2 v Coventry CityCoventry City 2-0 Chesterfield | Sky Bet League One |
| 18 | Sat 5 Nov 2016 | 52-1 v Colchester UnitedColchester United 1-2 Chesterfield | Emirates FA Cup First Round |
| 19 | Sun 13 Nov 2016 | 51-4 v Sheffield UnitedChesterfield 1-4 Sheffield United | Sky Bet League One |
| 20 | Sat 19 Nov 2016 | 51-2 v Fleetwood TownFleetwood Town 2-1 Chesterfield | Sky Bet League One |
| 21 | Tue 22 Nov 2016 | 53-2 v Milton Keynes DonsMilton Keynes Dons 2-3 Chesterfield | Sky Bet League One |
| 22 | Sat 26 Nov 2016 | 53-2 v Bristol RoversChesterfield 3-2 Bristol Rovers | Sky Bet League One |
| 23 | Sat 3 Dec 2016 | 50-5 v Wycombe WanderersChesterfield 0-5 Wycombe Wanderers | Emirates FA Cup Second Round |
| 24 | Tue 6 Dec 2016 | 52-0 v RochdaleRochdale 0-2 Chesterfield | Checkatrade Trophy Second Round |
| 25 | Sat 10 Dec 2016 | 52-5 v Peterborough UnitedPeterborough United 5-2 Chesterfield | Sky Bet League One |
| 26 | Sat 17 Dec 2016 | 51-0 v Bolton WanderersChesterfield 1-0 Bolton Wanderers | Sky Bet League One |
| 27 | Mon 26 Dec 2016 | 50-3 v RochdaleRochdale 3-0 Chesterfield | Sky Bet League One |
| 28 | Fri 30 Dec 2016 | 50-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League One |
| 29 | Mon 2 Jan 2017 | 50-0 v Milton Keynes DonsChesterfield 0-0 Milton Keynes Dons | Sky Bet League One |
| 30 | Sat 7 Jan 2017 | 50-2 v Bradford CityBradford City 2-0 Chesterfield | Sky Bet League One |
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