| 2000-02-26 | CheltenhamvPeterboroLeague Two · England | 2–1 | League Two · England |
| 2000-02-19 | Leyton OrientvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2000-02-13 | CheltenhamvSwanseaLeague Two · England | 0–0 | League Two · England |
| 2000-02-05 | BarnetvCheltenhamLeague Two · England | 3–2 | League Two · England |
| 2000-01-29 | CheltenhamvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 2000-01-22 | HullvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2000-01-15 | CheltenhamvMansfieldLeague Two · England | 1–0 | League Two · England |
| 2000-01-08 | MacclesfieldvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2000-01-03 | CheltenhamvLincolnLeague Two · England | 0–2 | League Two · England |
| 1999-12-28 | YorkvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | CheltenhamvExeterLeague Two · England | 3–1 | League Two · England |
| 1999-12-11 | CheltenhamvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1999-12-04 | RochdalevCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-27 | CheltenhamvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1999-11-23 | CheltenhamvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-11-16 | SwanseavCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | NorthamptonvCheltenhamLeague Two · England | 3–2 | League Two · England |
| 1999-11-06 | CheltenhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | HalifaxvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 1999-10-23 | CheltenhamvBrightonLeague Two · England | 0–0 | League Two · England |
| 1999-10-19 | ChestervCheltenhamLeague Two · England | 2–1 | League Two · England |
| 1999-10-16 | DarlingtonvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 1999-10-09 | CheltenhamvSouthendLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | CheltenhamvRotherhamLeague Two · England | 0–2 | League Two · England |
| 1999-09-25 | BrightonvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 1999-09-18 | PeterborovCheltenhamLeague Two · England | 1–0 | League Two · England |
| 1999-09-12 | CheltenhamvShrewsburyLeague Two · England | 0–1 | League Two · England |
| 1999-08-30 | CheltenhamvBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-08-28 | HartlepoolvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 1999-08-21 | CheltenhamvHullLeague Two · England | 1–0 | League Two · England |
| 1999-08-14 | MansfieldvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 1999-08-07 | CheltenhamvRochdaleLeague Two · England | 0–2 | League Two · England |