| 1999-09-03 | HullvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-08-30 | ChestervRochdaleLeague Two · England | 0–2 | League Two · England |
| 1999-08-28 | TorquayvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-08-18 | ChestervNorthamptonLeague Two · England | 0–2 | League Two · England |
| 1999-08-14 | RotherhamvChesterLeague Two · England | 4–0 | League Two · England |
| 1999-08-07 | ChestervBarnetLeague Two · England | 0–2 | League Two · England |
| 1999-05-08 | ChestervRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-05-01 | DarlingtonvChesterLeague Two · England | 1–2 | League Two · England |
| 1999-04-24 | ChestervHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-04-17 | RochdalevChesterLeague Two · England | 3–1 | League Two · England |
| 1999-04-13 | ChestervBrentfordLeague Two · England | 1–3 | League Two · England |
| 1999-04-10 | HartlepoolvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-04-05 | ChestervBarnetLeague Two · England | 3–0 | League Two · England |
| 1999-04-03 | SwanseavChesterLeague Two · England | 1–1 | League Two · England |
| 1999-03-27 | ChestervPlymouthLeague Two · England | 3–2 | League Two · England |
| 1999-03-20 | ShrewsburyvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-03-13 | ChestervScunthorpeLeague Two · England | 0–2 | League Two · England |
| 1999-03-09 | ChestervScarboroughLeague Two · England | 1–3 | League Two · England |
| 1999-03-05 | CardiffvChesterLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | ChestervCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-02-23 | PlymouthvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-02-20 | TorquayvChesterLeague Two · England | 0–3 | League Two · England |
| 1999-02-13 | ChestervPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-02-06 | ChestervExeterLeague Two · England | 0–0 | League Two · England |
| 1999-01-30 | MansfieldvChesterLeague Two · England | 3–0 | League Two · England |
| 1999-01-23 | CambridgevChesterLeague Two · England | 2–1 | League Two · England |
| 1999-01-15 | ChestervBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-01-09 | Leyton OrientvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-01-02 | ChestervSouthendLeague Two · England | 1–1 | League Two · England |
| 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 |