| 1 | Tue 7 Aug 2018 | 323-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 2 | Sat 11 Aug 2018 | 321-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 3 | Tue 14 Aug 2018 | 322-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | Sat 25 Aug 2018 | 320-1 v BarnetChesterfield 0-1 Barnet | National League |
| 5 | Mon 27 Aug 2018 | 320-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 6 | Tue 4 Sep 2018 | 320-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 7 | Tue 25 Sep 2018 | 321-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 8 | Sat 29 Sep 2018 | 321-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 9 | Sat 6 Oct 2018 | 320-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 10 | Sat 13 Oct 2018 | 321-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 11 | Sat 10 Nov 2018 | 321-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 12 | Sat 17 Nov 2018 | 320-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 13 | Tue 1 Jan 2019 | 322-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 14 | Sat 5 Jan 2019 | 323-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 15 | Sat 19 Jan 2019 | 322-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 16 | Sat 26 Jan 2019 | 320-0 v BarrowChesterfield 0-0 Barrow | National League |
| 17 | Sat 9 Feb 2019 | 321-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 18 | Sat 16 Feb 2019 | 321-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 19 | Sat 23 Feb 2019 | 320-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 20 | Sat 2 Mar 2019 | 320-1 v WrexhamWrexham 1-0 Chesterfield | National League |
| 21 | Tue 12 Mar 2019 | 323-3 v BromleyBromley 3-3 Chesterfield | National League |
| 22 | Sat 23 Mar 2019 | 323-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 23 | Sat 6 Apr 2019 | 320-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 24 | Fri 19 Apr 2019 | 320-1 v GatesheadGateshead 1-0 Chesterfield | National League |
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