| 2014-12-28 | CheltenhamvNewport CountyLeague Two · England | 0–1 | League Two · England |
| 2014-12-26 | ExetervCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2014-12-20 | CheltenhamvPortsmouthLeague Two · England | 1–1 | League Two · England |
| 2014-12-13 | MansfieldvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2014-11-29 | CheltenhamvOxfordLeague Two · England | 1–1 | League Two · England |
| 2014-11-22 | CheltenhamvWycombeLeague Two · England | 1–4 | League Two · England |
| 2014-11-15 | StevenagevCheltenhamLeague Two · England | 5–1 | League Two · England |
| 2014-11-01 | CheltenhamvYorkLeague Two · England | 0–1 | League Two · England |
| 2014-10-25 | PlymouthvCheltenhamLeague Two · England | 3–0 | League Two · England |
| 2014-10-21 | CambridgevCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2014-10-18 | CheltenhamvNorthamptonLeague Two · England | 3–2 | League Two · England |
| 2014-10-11 | ShrewsburyvCheltenhamLeague Two · England | 3–1 | League Two · England |
| 2014-10-04 | CheltenhamvAFC WimbledonLeague Two · England | 1–1 | League Two · England |
| 2014-09-27 | BurtonvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2014-09-20 | CheltenhamvDag and RedLeague Two · England | 1–1 | League Two · England |
| 2014-09-16 | CheltenhamvSouthendLeague Two · England | 0–1 | League Two · England |
| 2014-09-13 | LutonvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2014-09-06 | MorecambevCheltenhamLeague Two · England | 0–0 | League Two · England |
| 2014-08-30 | CheltenhamvHartlepoolLeague Two · England | 1–0 | League Two · England |
| 2014-08-23 | TranmerevCheltenhamLeague Two · England | 2–3 | League Two · England |
| 2014-08-19 | CheltenhamvCarlisleLeague Two · England | 0–0 | League Two · England |
| 2014-08-16 | CheltenhamvAccringtonLeague Two · England | 2–1 | League Two · England |
| 2014-08-09 | BuryvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2014-05-03 | CheltenhamvDag and RedLeague Two · England | 2–3 | League Two · England |
| 2014-04-26 | RochdalevCheltenhamLeague Two · England | 2–0 | League Two · England |
| 2014-04-21 | MansfieldvCheltenhamLeague Two · England | 0–2 | League Two · England |
| 2014-04-18 | CheltenhamvFleetwood TownLeague Two · England | 1–2 | League Two · England |
| 2014-04-12 | ExetervCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2014-04-05 | CheltenhamvSouthendLeague Two · England | 1–2 | League Two · England |
| 2014-03-29 | HartlepoolvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2014-03-25 | CheltenhamvScunthorpeLeague Two · England | 0–2 | League Two · England |
| 2014-03-22 | AFC WimbledonvCheltenhamLeague Two · England | 4–3 | League Two · England |
| 2014-03-18 | CheltenhamvWycombeLeague Two · England | 1–1 | League Two · England |
| 2014-03-15 | CheltenhamvTorquayLeague Two · England | 1–0 | League Two · England |
| 2014-03-11 | OxfordvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2014-03-08 | PortsmouthvCheltenhamLeague Two · England | 0–0 | League Two · England |
| 2014-03-01 | CheltenhamvBuryLeague Two · England | 2–1 | League Two · England |
| 2014-02-25 | CheltenhamvChesterfieldLeague Two · England | 1–4 | League Two · England |
| 2014-02-22 | Newport CountyvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2014-02-11 | Bristol RvsvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2014-02-08 | YorkvCheltenhamLeague Two · England | 0–0 | League Two · England |
| 2014-02-01 | CheltenhamvNorthamptonLeague Two · England | 1–1 | League Two · England |
| 2014-01-25 | PlymouthvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2014-01-18 | CheltenhamvAccringtonLeague Two · England | 1–2 | League Two · England |
| 2014-01-11 | BurtonvCheltenhamLeague Two · England | 2–1 | League Two · England |