| 2018-12-29 | ChesterfieldvHartlepoolNational League · England | 1–1 | National League · England |
| 2018-12-26 | ChesterfieldvSolihullNational League · England | 0–4 | National League · England |
| 2018-12-22 | Leyton OrientvChesterfieldNational League · England | 3–1 | National League · England |
| 2018-12-08 | ChesterfieldvSalfordNational League · England | 2–0 | National League · England |
| 2018-11-27 | ChesterfieldvBromleyNational League · England | 1–1 | National League · England |
| 2018-11-24 | EastleighvChesterfieldNational League · England | 1–1 | National League · England |
| 2018-11-17 | ChesterfieldvHavant & WaterloovilleNational League · England | 0–0 | National League · England |
| 2018-11-03 | HarrogatevChesterfieldNational League · England | 1–1 | National League · England |
| 2018-10-30 | SuttonvChesterfieldNational League · England | 1–1 | National League · England |
| 2018-10-27 | ChesterfieldvWrexhamNational League · England | 1–1 | National League · England |
| 2018-10-13 | HalifaxvChesterfieldNational League · England | 1–1 | National League · England |
| 2018-10-06 | ChesterfieldvFyldeNational League · England | 0–0 | National League · England |
| 2018-09-29 | MaidstonevChesterfieldNational League · England | 1–1 | National League · England |
| 2018-09-25 | ChesterfieldvMaidenheadNational League · England | 1–3 | National League · England |
| 2018-09-22 | ChesterfieldvGatesheadNational League · England | 0–3 | National League · England |
| 2018-09-15 | Dag and RedvChesterfieldNational League · England | 1–1 | National League · England |
| 2018-09-08 | ChesterfieldvDover AthleticNational League · England | 0–0 | National League · England |
| 2018-09-04 | Boreham WoodvChesterfieldNational League · England | 1–0 | National League · England |
| 2018-09-01 | ChesterfieldvLeyton OrientNational League · England | 0–1 | National League · England |
| 2018-08-27 | HartlepoolvChesterfieldNational League · England | 1–0 | National League · England |
| 2018-08-25 | ChesterfieldvBarnetNational League · England | 0–1 | National League · England |
| 2018-08-18 | SalfordvChesterfieldNational League · England | 3–2 | National League · England |
| 2018-08-14 | BarrowvChesterfieldNational League · England | 3–2 | National League · England |
| 2018-08-11 | ChesterfieldvBraintree TownNational League · England | 1–0 | National League · England |
| 2018-08-07 | ChesterfieldvAldershotNational League · England | 3–0 | National League · England |
| 2018-08-04 | EbbsfleetvChesterfieldNational League · England | 0–1 | National League · England |