| 1 | Sat 4 Aug 2018 | 21-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield | National League |
| 2 | Sat 11 Aug 2018 | 21-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 3 | Sat 25 Aug 2018 | 20-1 v BarnetChesterfield 0-1 Barnet | National League |
| 4 | Tue 4 Sep 2018 | 20-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 5 | Sat 8 Sep 2018 | 2 0-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 6 | Sat 15 Sep 2018 | 21-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 7 | Sat 24 Nov 2018 | 1-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 8 | Tue 27 Nov 2018 | 21-1 v BromleyChesterfield 1-1 Bromley | National League |
| 9 | Sun 2 Dec 2018 | 20-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 10 | Sat 8 Dec 2018 | 2 2-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 11 | Sat 29 Dec 2018 | 21-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 12 | Tue 1 Jan 2019 | 22-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 13 | Sat 5 Jan 2019 | 23-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 14 | Sat 19 Jan 2019 | 2 2-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 15 | Sat 26 Jan 2019 | 20-0 v BarrowChesterfield 0-0 Barrow | National League |
| 16 | Sat 16 Mar 2019 | 22-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 17 | Sat 6 Apr 2019 | 20-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 18 | Sat 13 Apr 2019 | 24-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 19 | Fri 19 Apr 2019 | 20-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 20 | Mon 22 Apr 2019 | 23-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 21 | Sat 27 Apr 2019 | 20-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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