| 1 | Sat 28 Jul 2018 | 0-2 v Alfreton TownAlfreton Town 2-0 Chesterfield | Friendly |
| 2 | Tue 7 Aug 2018 | 3-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 3 | Tue 14 Aug 2018 | 2-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | Mon 27 Aug 2018 | 0-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 5 | Tue 4 Sep 2018 | 0-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 6 | Sat 8 Sep 2018 | 0-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 7 | Sat 15 Sep 2018 | 1-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 8 | Sat 22 Sep 2018 | 0-3 v GatesheadChesterfield 0-3 Gateshead | National League |
| 9 | Tue 25 Sep 2018 | 1-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 10 | Sat 29 Sep 2018 | 1-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 11 | Sat 6 Oct 2018 | 0-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 12 | Sat 13 Oct 2018 | 1-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 13 | Sat 27 Oct 2018 | 1-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 14 | Tue 30 Oct 2018 | 1-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 15 | Sat 3 Nov 2018 | 1-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 16 | Sat 10 Nov 2018 | 1-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 17 | Sat 17 Nov 2018 | 0-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 18 | Tue 20 Nov 2018 | 3-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 19 | Sat 24 Nov 2018 | 1-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 20 | Sun 2 Dec 2018 | 0-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 21 | Sat 8 Dec 2018 | 2-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 22 | Sat 22 Dec 2018 | 1-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
| 23 | Wed 26 Dec 2018 | 0-4 v Solihull MoorsChesterfield 0-4 Solihull Moors | National League |
| 24 | Sat 29 Dec 2018 | 1-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 25 | Tue 1 Jan 2019 | 2-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 26 | Sat 5 Jan 2019 | 3-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 27 | Sat 19 Jan 2019 | 2-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 28 | Sat 26 Jan 2019 | 0-0 v BarrowChesterfield 0-0 Barrow | National League |
| 29 | Sat 9 Feb 2019 | 1-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 30 | Sat 16 Feb 2019 | 1-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 31 | Sat 23 Feb 2019 | 0-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 32 | Tue 5 Mar 2019 | 3-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 33 | Tue 12 Mar 2019 | 3-3 v BromleyBromley 3-3 Chesterfield | National League |
| 34 | Sat 30 Mar 2019 | 2-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 35 | Sat 6 Apr 2019 | 0-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 36 | Mon 22 Apr 2019 | 3-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 37 | Sat 27 Apr 2019 | 0-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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