| 1998-12-28 | ChestervMansfieldLeague Two · England | 1–1 | League Two · England |
| 1998-12-26 | HullvChesterLeague Two · England | 1–2 | League Two · England |
| 1998-12-18 | RotherhamvChesterLeague Two · England | 2–4 | League Two · England |
| 1998-12-12 | ChestervDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1998-11-28 | BrentfordvChesterLeague Two · England | 2–1 | League Two · England |
| 1998-11-21 | ChestervRochdaleLeague Two · England | 1–1 | League Two · England |
| 1998-11-10 | HalifaxvChesterLeague Two · England | 3–2 | League Two · England |
| 1998-11-07 | ScunthorpevChesterLeague Two · England | 2–1 | League Two · England |
| 1998-10-31 | ChestervShrewsburyLeague Two · England | 1–1 | League Two · England |
| 1998-10-20 | ChestervHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1998-10-17 | ChestervSwanseaLeague Two · England | 1–1 | League Two · England |
| 1998-10-11 | BarnetvChesterLeague Two · England | 0–0 | League Two · England |
| 1998-10-03 | ScarboroughvChesterLeague Two · England | 2–4 | League Two · England |
| 1998-09-27 | ChestervCardiffLeague Two · England | 2–2 | League Two · England |
| 1998-09-19 | CarlislevChesterLeague Two · England | 1–1 | League Two · England |
| 1998-09-12 | ChestervTorquayLeague Two · England | 2–0 | League Two · England |
| 1998-09-08 | PeterborovChesterLeague Two · England | 3–0 | League Two · England |
| 1998-09-05 | ExetervChesterLeague Two · England | 0–1 | League Two · England |
| 1998-09-01 | ChestervCambridgeLeague Two · England | 0–3 | League Two · England |
| 1998-08-29 | SouthendvChesterLeague Two · England | 0–1 | League Two · England |
| 1998-08-23 | ChestervHullLeague Two · England | 2–2 | League Two · England |
| 1998-08-15 | BrightonvChesterLeague Two · England | 2–2 | League Two · England |
| 1998-08-08 | ChestervLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 1998-05-02 | ChestervScarboroughLeague Two · England | 1–1 | League Two · England |
| 1998-04-25 | MacclesfieldvChesterLeague Two · England | 3–2 | League Two · England |
| 1998-04-18 | ChestervColchesterLeague Two · England | 3–1 | League Two · England |
| 1998-04-13 | DarlingtonvChesterLeague Two · England | 1–0 | League Two · England |
| 1998-04-11 | ChestervDoncasterLeague Two · England | 2–1 | League Two · England |
| 1998-04-04 | ExetervChesterLeague Two · England | 5–0 | League Two · England |
| 1998-03-29 | SwanseavChesterLeague Two · England | 2–0 | League Two · England |
| 1998-03-21 | PeterborovChesterLeague Two · England | 2–1 | League Two · England |
| 1998-03-14 | ChestervNotts CountyLeague Two · England | 0–1 | League Two · England |
| 1998-03-07 | RochdalevChesterLeague Two · England | 1–1 | League Two · England |
| 1998-03-03 | ChestervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-02-28 | BrightonvChesterLeague Two · England | 3–2 | League Two · England |
| 1998-02-24 | ChestervTorquayLeague Two · England | 1–3 | League Two · England |
| 1998-02-21 | ChestervRotherhamLeague Two · England | 4–0 | League Two · England |
| 1998-02-14 | HartlepoolvChesterLeague Two · England | 0–0 | League Two · England |
| 1998-02-07 | ChestervMansfieldLeague Two · England | 0–1 | League Two · England |
| 1998-01-31 | ShrewsburyvChesterLeague Two · England | 1–1 | League Two · England |
| 1998-01-27 | ChestervCardiffLeague Two · England | 0–0 | League Two · England |
| 1998-01-24 | CambridgevChesterLeague Two · England | 1–2 | League Two · England |
| 1998-01-17 | ChestervBarnetLeague Two · England | 0–1 | League Two · England |
| 1998-01-10 | LincolnvChesterLeague Two · England | 1–3 | League Two · England |