| 2009-05-02 | SouthendvCheltenhamLeague One · England | 2–0 | League One · England |
| 2009-04-28 | ScunthorpevCheltenhamLeague One · England | 3–0 | League One · England |
| 2009-04-25 | CheltenhamvCarlisleLeague One · England | 1–1 | League One · England |
| 2009-04-18 | CrewevCheltenhamLeague One · England | 1–2 | League One · England |
| 2009-04-13 | CheltenhamvYeovilLeague One · England | 1–0 | League One · England |
| 2009-04-10 | PeterborovCheltenhamLeague One · England | 1–1 | League One · England |
| 2009-04-04 | CheltenhamvLeyton OrientLeague One · England | 0–1 | League One · England |
| 2009-03-28 | WalsallvCheltenhamLeague One · England | 1–1 | League One · England |
| 2009-03-24 | CheltenhamvOldhamLeague One · England | 1–1 | League One · England |
| 2009-03-21 | HuddersfieldvCheltenhamLeague One · England | 2–2 | League One · England |
| 2009-03-17 | CheltenhamvTranmereLeague One · England | 1–0 | League One · England |
| 2009-03-14 | CheltenhamvHartlepoolLeague One · England | 2–0 | League One · England |
| 2009-03-07 | LeicestervCheltenhamLeague One · England | 4–0 | League One · England |
| 2009-03-03 | SwindonvCheltenhamLeague One · England | 2–2 | League One · England |
| 2009-02-28 | CheltenhamvNorthamptonLeague One · England | 0–1 | League One · England |
| 2009-02-24 | CheltenhamvMillwallLeague One · England | 1–3 | League One · England |
| 2009-02-21 | LeedsvCheltenhamLeague One · England | 2–0 | League One · England |
| 2009-02-17 | StockportvCheltenhamLeague One · England | 1–0 | League One · England |
| 2009-02-14 | CheltenhamvHerefordLeague One · England | 2–3 | League One · England |
| 2009-01-31 | CheltenhamvMilton Keynes DonsLeague One · England | 3–5 | League One · England |
| 2009-01-27 | Bristol RvsvCheltenhamLeague One · England | 3–2 | League One · England |
| 2009-01-24 | CheltenhamvBrightonLeague One · England | 2–2 | League One · England |
| 2009-01-17 | ColchestervCheltenhamLeague One · England | 3–1 | League One · England |