| 1 | Sat 9 Feb 2019 | 1-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 2 | Sat 16 Feb 2019 | 1-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 3 | Sat 23 Feb 2019 | 0-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 4 | Tue 26 Feb 2019 | 2-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 5 | Sat 2 Mar 2019 | 0-1 v WrexhamWrexham 1-0 Chesterfield | National League |
| 6 | Tue 5 Mar 2019 | 3-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 7 | Sat 9 Mar 2019 | 2-3 v EastleighChesterfield 2-3 Eastleigh | National League |
| 8 | Sat 16 Mar 2019 | 2-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 9 | Sat 23 Mar 2019 | 3-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 10 | Sat 30 Mar 2019 | 2-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 11 | Sat 13 Apr 2019 | 4-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 12 | Fri 19 Apr 2019 | 0-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 13 | Mon 22 Apr 2019 | 3-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 14 | Sat 27 Apr 2019 | 0-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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