| 1 | Sat 28 Jul 2018 | 250-2 v Alfreton TownAlfreton Town 2-0 Chesterfield | Friendly |
| 2 | Sat 4 Aug 2018 | 251-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield | National League |
| 3 | Tue 7 Aug 2018 | 253-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 4 | Sat 11 Aug 2018 | 251-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 5 | Tue 14 Aug 2018 | 252-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 6 | Sat 25 Aug 2018 | 250-1 v BarnetChesterfield 0-1 Barnet | National League |
| 7 | Mon 27 Aug 2018 | 250-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 8 | Sat 1 Sep 2018 | 250-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 9 | Tue 4 Sep 2018 | 25 0-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 10 | Sat 8 Sep 2018 | 250-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 11 | Sat 15 Sep 2018 | 251-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 12 | Sat 22 Sep 2018 | 250-3 v GatesheadChesterfield 0-3 Gateshead | National League |
| 13 | Tue 25 Sep 2018 | 25 1-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
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