| 2009-12-28 | Dag and RedvCheltenhamLeague Two · England | 0–2 | League Two · England |
| 2009-12-26 | CheltenhamvBournemouthLeague Two · England | 0–1 | League Two · England |
| 2009-12-12 | ChesterfieldvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2009-12-05 | CheltenhamvNorthamptonLeague Two · England | 2–2 | League Two · England |
| 2009-12-01 | TorquayvCheltenhamLeague Two · England | 3–0 | League Two · England |
| 2009-11-24 | CheltenhamvBarnetLeague Two · England | 5–1 | League Two · England |
| 2009-11-21 | MorecambevCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2009-11-14 | LincolnvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2009-10-31 | CheltenhamvCreweLeague Two · England | 0–4 | League Two · England |
| 2009-10-24 | Port ValevCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2009-10-16 | CheltenhamvMacclesfieldLeague Two · England | 1–2 | League Two · England |
| 2009-10-10 | AccringtonvCheltenhamLeague Two · England | 4–0 | League Two · England |
| 2009-10-03 | CheltenhamvNotts CountyLeague Two · England | 1–1 | League Two · England |
| 2009-09-29 | CheltenhamvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 2009-09-26 | AldershotvCheltenhamLeague Two · England | 4–1 | League Two · England |
| 2009-09-19 | CheltenhamvRotherhamLeague Two · England | 1–1 | League Two · England |
| 2009-09-12 | BuryvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2009-09-05 | CheltenhamvDag and RedLeague Two · England | 1–1 | League Two · England |
| 2009-08-29 | DarlingtonvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2009-08-22 | CheltenhamvBradfordLeague Two · England | 4–5 | League Two · England |
| 2009-08-18 | RochdalevCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2009-08-15 | HerefordvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2009-08-08 | CheltenhamvGrimsbyLeague Two · England | 2–1 | League Two · England |