| 1998-12-28 | CarlislevCambridgeLeague Two · England | 1–1 | League Two · England |
| 1998-12-26 | RochdalevCarlisleLeague Two · England | 1–1 | League Two · England |
| 1998-12-19 | PlymouthvCarlisleLeague Two · England | 2–0 | League Two · England |
| 1998-12-12 | CarlislevHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-12-01 | CarlislevCardiffLeague Two · England | 0–1 | League Two · England |
| 1998-11-28 | HullvCarlisleLeague Two · England | 1–0 | League Two · England |
| 1998-11-21 | CarlislevRotherhamLeague Two · England | 0–0 | League Two · England |
| 1998-11-07 | CarlislevHalifaxLeague Two · England | 0–1 | League Two · England |
| 1998-10-20 | PeterborovCarlisleLeague Two · England | 0–1 | League Two · England |
| 1998-10-17 | TorquayvCarlisleLeague Two · England | 2–2 | League Two · England |
| 1998-10-09 | CarlislevScarboroughLeague Two · England | 1–0 | League Two · England |
| 1998-10-03 | CarlislevBarnetLeague Two · England | 2–1 | League Two · England |
| 1998-09-27 | ShrewsburyvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1998-09-19 | CarlislevChesterLeague Two · England | 1–1 | League Two · England |
| 1998-09-12 | MansfieldvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1998-09-08 | CarlislevSwanseaLeague Two · England | 1–2 | League Two · England |
| 1998-09-05 | Leyton OrientvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1998-09-01 | CarlislevSouthendLeague Two · England | 3–0 | League Two · England |
| 1998-08-29 | ExetervCarlisleLeague Two · England | 2–0 | League Two · England |
| 1998-08-22 | CarlislevRochdaleLeague Two · England | 0–1 | League Two · England |
| 1998-08-15 | ScunthorpevCarlisleLeague Two · England | 3–1 | League Two · England |
| 1998-08-08 | CarlislevBrightonLeague Two · England | 1–0 | League Two · England |