| 2006-05-06 | MansfieldvCheltenhamLeague Two · England | 0–5 | League Two · England |
| 2006-04-29 | CheltenhamvNotts CountyLeague Two · England | 2–0 | League Two · England |
| 2006-04-21 | GrimsbyvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2006-04-17 | CheltenhamvDarlingtonLeague Two · England | 1–1 | League Two · England |
| 2006-04-15 | TorquayvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2006-04-08 | CheltenhamvStockportLeague Two · England | 3–3 | League Two · England |
| 2006-04-01 | ShrewsburyvCheltenhamLeague Two · England | 2–0 | League Two · England |
| 2006-03-25 | CheltenhamvRushden & DLeague Two · England | 3–1 | League Two · England |
| 2006-03-21 | CheltenhamvWrexhamLeague Two · England | 2–2 | League Two · England |
| 2006-03-18 | ChestervCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2006-03-11 | Leyton OrientvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2006-03-04 | CheltenhamvWycombeLeague Two · England | 2–1 | League Two · England |
| 2006-02-25 | CheltenhamvRochdaleLeague Two · England | 1–1 | League Two · England |
| 2006-02-18 | OxfordvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2006-02-14 | Bristol RvsvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2006-02-11 | CheltenhamvNorthamptonLeague Two · England | 3–1 | League Two · England |
| 2006-02-04 | PeterborovCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2006-01-21 | CarlislevCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2006-01-14 | CheltenhamvBristol RvsLeague Two · England | 2–3 | League Two · England |
| 2006-01-10 | BarnetvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2006-01-02 | StockportvCheltenhamLeague Two · England | 2–2 | League Two · England |