| 1999-12-28 | ChestervLeyton OrientLeague Two · England | 1–5 | League Two · England |
| 1999-12-26 | MansfieldvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | ChestervHalifaxLeague Two · England | 2–1 | League Two · England |
| 1999-12-15 | DarlingtonvChesterLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | BarnetvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-11-27 | ChestervSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | ChestervSouthendLeague Two · England | 0–0 | League Two · England |
| 1999-11-13 | HartlepoolvChesterLeague Two · England | 1–0 | League Two · England |
| 1999-11-06 | ChestervPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-11-02 | ShrewsburyvChesterLeague Two · England | 0–1 | League Two · England |
| 1999-10-23 | LincolnvChesterLeague Two · England | 4–1 | League Two · England |
| 1999-10-19 | ChestervCheltenhamLeague Two · England | 2–1 | League Two · England |
| 1999-10-16 | ChestervMacclesfieldLeague Two · England | 1–2 | League Two · England |
| 1999-10-09 | PeterborovChesterLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | YorkvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-09-25 | ChestervLincolnLeague Two · England | 1–3 | League Two · England |
| 1999-09-18 | BrightonvChesterLeague Two · England | 2–3 | League Two · England |
| 1999-09-11 | ChestervExeterLeague Two · England | 1–1 | League Two · England |
| 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 |