| 2000-01-22 | HartlepoolvCarlisleLeague Two · England | 1–0 | League Two · England |
| 2000-01-08 | TorquayvCarlisleLeague Two · England | 4–1 | League Two · England |
| 2000-01-03 | CarlislevChesterLeague Two · England | 4–1 | League Two · England |
| 1999-12-28 | MacclesfieldvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | CarlislevRochdaleLeague Two · England | 1–2 | League Two · England |
| 1999-12-18 | HullvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-14 | CarlislevTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | Leyton OrientvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | CarlislevRotherhamLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | BarnetvCarlisleLeague Two · England | 3–0 | League Two · England |
| 1999-11-12 | CarlislevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | CheltenhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | CarlislevYorkLeague Two · England | 0–1 | League Two · England |
| 1999-10-23 | CarlislevHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-10-19 | DarlingtonvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-10-16 | ExetervCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-10-09 | CarlislevBrightonLeague Two · England | 0–1 | League Two · England |
| 1999-10-02 | CarlislevSouthendLeague Two · England | 1–1 | League Two · England |
| 1999-09-25 | HalifaxvCarlisleLeague Two · England | 5–2 | League Two · England |
| 1999-09-18 | ShrewsburyvCarlisleLeague Two · England | 4–1 | League Two · England |
| 1999-09-11 | CarlislevLincolnLeague Two · England | 1–0 | League Two · England |
| 1999-09-04 | NorthamptonvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-08-30 | CarlislevPlymouthLeague Two · England | 4–2 | League Two · England |
| 1999-08-28 | MansfieldvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-08-21 | CarlislevHartlepoolLeague Two · England | 0–3 | League Two · England |
| 1999-08-14 | SwanseavCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-08-07 | CarlislevLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | CarlislevPlymouthLeague Two · England | 2–1 | League Two · England |
| 1999-05-01 | HartlepoolvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-04-24 | CarlislevDarlingtonLeague Two · England | 3–3 | League Two · England |
| 1999-04-17 | RotherhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-04-13 | CarlislevHullLeague Two · England | 0–0 | League Two · England |
| 1999-04-10 | CarlislevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-05 | ScarboroughvCarlisleLeague Two · England | 3–0 | League Two · England |
| 1999-04-03 | CarlislevTorquayLeague Two · England | 3–0 | League Two · England |
| 1999-03-27 | CardiffvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-03-23 | DarlingtonvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-03-20 | CarlislevBrentfordLeague Two · England | 0–1 | League Two · England |
| 1999-03-13 | HalifaxvCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-03-09 | BarnetvCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-03-06 | CarlislevShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1999-02-27 | ChestervCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-02-20 | CarlislevMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-02-13 | SwanseavCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-02-06 | CarlislevLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-02-02 | BrentfordvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-01-30 | CambridgevCarlisleLeague Two · England | 1–0 | League Two · England |
| 1999-01-23 | SouthendvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-01-16 | CarlislevScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1999-01-09 | BrightonvCarlisleLeague Two · England | 1–3 | League Two · England |