| 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 |
| 2018-05-05 | BarnetvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2018-05-01 | ChesterfieldvNewport CountyLeague Two · England | 1–0 | League Two · England |
| 2018-04-28 | ChesterfieldvWycombeLeague Two · England | 1–2 | League Two · England |
| 2018-04-21 | Forest GreenvChesterfieldLeague Two · England | 4–1 | League Two · England |
| 2018-04-17 | ExetervChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2018-04-14 | ChesterfieldvMansfieldLeague Two · England | 0–1 | League Two · England |
| 2018-04-10 | MorecambevChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2018-04-07 | GrimsbyvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2018-03-30 | Port ValevChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2018-03-25 | ChesterfieldvNotts CountyLeague Two · England | 3–1 | League Two · England |
| 2018-03-17 | CheltenhamvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2018-03-10 | ChesterfieldvLincolnLeague Two · England | 1–3 | League Two · England |
| 2018-02-24 | ChesterfieldvSwindonLeague Two · England | 2–1 | League Two · England |
| 2018-02-17 | CarlislevChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2018-02-13 | ChesterfieldvCambridgeLeague Two · England | 2–3 | League Two · England |
| 2018-02-03 | ChesterfieldvCrawley TownLeague Two · England | 1–2 | League Two · England |
| 2018-01-27 | ChesterfieldvStevenageLeague Two · England | 0–1 | League Two · England |
| 2018-01-20 | YeovilvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2018-01-13 | ChesterfieldvLutonLeague Two · England | 2–0 | League Two · England |
| 2018-01-06 | AccringtonvChesterfieldLeague Two · England | 4–0 | League Two · England |
| 2018-01-01 | CoventryvChesterfieldLeague Two · England | 1–0 | League Two · England |