| 1998-12-28 | WycombevChesterfieldLeague One · England | 1–0 | League One · England |
| 1998-12-26 | ChesterfieldvOldhamLeague One · England | 1–3 | League One · England |
| 1998-12-19 | ChesterfieldvWiganLeague One · England | 1–1 | League One · England |
| 1998-12-12 | NorthamptonvChesterfieldLeague One · England | 1–0 | League One · England |
| 1998-12-05 | BlackpoolvChesterfieldLeague One · England | 1–1 | League One · England |
| 1998-11-28 | ChesterfieldvMacclesfieldLeague One · England | 2–0 | League One · England |
| 1998-11-21 | FulhamvChesterfieldLeague One · England | 2–1 | League One · England |
| 1998-11-10 | ChesterfieldvBournemouthLeague One · England | 3–1 | League One · England |
| 1998-11-07 | ChesterfieldvLincolnLeague One · England | 3–0 | League One · England |
| 1998-10-20 | ChesterfieldvNotts CountyLeague One · England | 3–0 | League One · England |
| 1998-10-17 | ChesterfieldvYorkLeague One · England | 2–1 | League One · England |
| 1998-10-12 | StokevChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-10-03 | MillwallvChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-09-27 | ChesterfieldvWrexhamLeague One · England | 2–1 | League One · England |
| 1998-09-19 | Man CityvChesterfieldLeague One · England | 1–1 | League One · England |
| 1998-09-12 | ChesterfieldvWalsallLeague One · England | 0–1 | League One · England |
| 1998-09-08 | Bristol RvsvChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-09-05 | ChesterfieldvGillinghamLeague One · England | 1–0 | League One · England |
| 1998-08-31 | PrestonvChesterfieldLeague One · England | 2–0 | League One · England |
| 1998-08-29 | ChesterfieldvReadingLeague One · England | 1–0 | League One · England |
| 1998-08-22 | OldhamvChesterfieldLeague One · England | 2–0 | League One · England |
| 1998-08-15 | ChesterfieldvBurnleyLeague One · England | 1–0 | League One · England |
| 1998-08-08 | ColchestervChesterfieldLeague One · England | 1–0 | League One · England |
| 1998-05-02 | ChesterfieldvBlackpoolLeague One · England | 1–1 | League One · England |
| 1998-04-25 | WycombevChesterfieldLeague One · England | 1–1 | League One · England |
| 1998-04-18 | ChesterfieldvBristol CityLeague One · England | 1–0 | League One · England |
| 1998-04-14 | LutonvChesterfieldLeague One · England | 3–0 | League One · England |
| 1998-04-11 | ChesterfieldvNorthamptonLeague One · England | 2–1 | League One · England |
| 1998-04-03 | SouthendvChesterfieldLeague One · England | 0–2 | League One · England |
| 1998-03-28 | ChesterfieldvMillwallLeague One · England | 3–1 | League One · England |
| 1998-03-21 | ChesterfieldvCarlisleLeague One · England | 2–1 | League One · England |
| 1998-03-14 | GillinghamvChesterfieldLeague One · England | 1–0 | League One · England |
| 1998-03-07 | ChesterfieldvFulhamLeague One · England | 0–2 | League One · England |
| 1998-03-03 | GrimsbyvChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-02-28 | WiganvChesterfieldLeague One · England | 2–1 | League One · England |
| 1998-02-24 | ChesterfieldvOldhamLeague One · England | 2–1 | League One · England |
| 1998-02-21 | ChesterfieldvWrexhamLeague One · England | 3–1 | League One · England |
| 1998-02-14 | BournemouthvChesterfieldLeague One · England | 2–0 | League One · England |
| 1998-02-07 | Bristol RvsvChesterfieldLeague One · England | 3–1 | League One · England |
| 1998-01-31 | ChesterfieldvWatfordLeague One · England | 0–1 | League One · England |
| 1998-01-24 | PrestonvChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-01-17 | ChesterfieldvPlymouthLeague One · England | 2–1 | League One · England |
| 1998-01-10 | WalsallvChesterfieldLeague One · England | 3–2 | League One · England |
| 1998-01-03 | ChesterfieldvBrentfordLeague One · England | 0–0 | League One · England |