| 1 | Sat 28 Jul 2018 | 60-2 v Alfreton TownAlfreton Town 2-0 Chesterfield | Friendly |
| 2 | Tue 7 Aug 2018 | 63-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 3 | Tue 14 Aug 2018 | 62-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | Sat 25 Aug 2018 | 60-1 v BarnetChesterfield 0-1 Barnet | National League |
| 5 | Sat 1 Sep 2018 | 60-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 6 | Tue 4 Sep 2018 | 60-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 7 | Sat 8 Sep 2018 | 60-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 8 | Sat 15 Sep 2018 | 61-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 9 | Tue 25 Sep 2018 | 61-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 10 | Sat 29 Sep 2018 | 61-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 11 | Sat 6 Oct 2018 | 60-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 12 | Sat 13 Oct 2018 | 61-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 13 | Sat 27 Oct 2018 | 61-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 14 | Tue 30 Oct 2018 | 61-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 15 | Sat 3 Nov 2018 | 61-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 16 | Sat 10 Nov 2018 | 61-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 17 | Sat 17 Nov 2018 | 60-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 18 | Tue 20 Nov 2018 | 6 3-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 19 | Sat 24 Nov 2018 | 61-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 20 | Tue 27 Nov 2018 | 61-1 v BromleyChesterfield 1-1 Bromley | National League |
| 21 | Sat 23 Feb 2019 | 60-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 22 | Tue 5 Mar 2019 | 63-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 23 | Sat 23 Mar 2019 | 63-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 24 | Sat 30 Mar 2019 | 62-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 25 | Sat 6 Apr 2019 | 60-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 26 | Sat 13 Apr 2019 | 64-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 27 | Fri 19 Apr 2019 | 60-1 v GatesheadGateshead 1-0 Chesterfield | National League |
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