| 1 | Tue 7 Aug 2018 | 3-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 2 | Sat 11 Aug 2018 | 1-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 3 | Tue 14 Aug 2018 | 2-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | Sat 22 Sep 2018 | 0-3 v GatesheadChesterfield 0-3 Gateshead | National League |
| 5 | Tue 25 Sep 2018 | 1-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 6 | Sat 29 Sep 2018 | 1-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 7 | Sat 23 Feb 2019 | 0-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 8 | Tue 26 Feb 2019 | 2-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 9 | Tue 5 Mar 2019 | 3-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 10 | Sat 9 Mar 2019 | 2-3 v EastleighChesterfield 2-3 Eastleigh | National League |
| 11 | Sat 23 Mar 2019 | 3-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 12 | Sat 30 Mar 2019 | 2-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 13 | Sat 6 Apr 2019 | 0-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 14 | Sat 13 Apr 2019 | 4-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 15 | Fri 19 Apr 2019 | 0-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 16 | Mon 22 Apr 2019 | 3-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 17 | Sat 27 Apr 2019 | 0-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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