| 1 | Sat 31 Aug | 120-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 2 | Tue 3 Sep | 121-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 3 | Fri 18 Oct | 123-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 4 | Tue 12 Nov | 123-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 5 | Sat 23 Nov | 12 1-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 6 | Sat 30 Nov | 120-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 7 | Tue 3 Dec | 120-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 8 | Sat 7 Dec | 123-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 9 | Sat 14 Dec | 122-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 1 Feb | 120-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 11 | Thu 6 Feb | 125-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 12 | Sat 15 Feb | 121-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 13 | Sat 22 Feb | 120-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
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