| 1 | Sat 25 Aug 2018 | 220-1 v BarnetChesterfield 0-1 Barnet | National League |
| 2 | Mon 27 Aug 2018 | 220-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 3 | Sat 15 Sep 2018 | 221-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 4 | Tue 25 Sep 2018 | 221-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 5 | Sat 29 Sep 2018 | 221-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 6 | Sat 6 Oct 2018 | 220-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 7 | Sat 13 Oct 2018 | 221-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 8 | Sat 27 Oct 2018 | 221-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 9 | Tue 30 Oct 2018 | 22 1-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 10 | Sat 3 Nov 2018 | 221-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 11 | Tue 20 Nov 2018 | 22 3-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 12 | Sat 22 Dec 2018 | 221-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
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