| 1 | Sat 13 Oct 2018 | 1-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 2 | Sat 27 Oct 2018 | 361-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 3 | Tue 30 Oct 2018 | 361-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 4 | Sat 3 Nov 2018 | 361-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 5 | Tue 20 Nov 2018 | 363-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 6 | Sun 2 Dec 2018 | 360-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 7 | Sat 8 Dec 2018 | 362-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 8 | Sat 22 Dec 2018 | 361-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
| 9 | Sat 19 Jan 2019 | 362-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 10 | Sat 26 Jan 2019 | 360-0 v BarrowChesterfield 0-0 Barrow | National League |
| 11 | Tue 26 Feb 2019 | 362-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 12 | Sat 6 Apr 2019 | 360-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 13 | Fri 19 Apr 2019 | 360-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 14 | Sat 27 Apr 2019 | 360-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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