| 2016-12-30 | CheltenhamvWycombeLeague Two · England | 0–1 | League Two · England |
| 2016-12-26 | CheltenhamvBarnetLeague Two · England | 1–2 | League Two · England |
| 2016-12-17 | MorecambevCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2016-12-10 | CheltenhamvExeterLeague Two · England | 1–3 | League Two · England |
| 2016-11-26 | CambridgevCheltenhamLeague Two · England | 3–1 | League Two · England |
| 2016-11-22 | CheltenhamvColchesterLeague Two · England | 0–3 | League Two · England |
| 2016-11-19 | CheltenhamvPortsmouthLeague Two · England | 1–1 | League Two · England |
| 2016-11-12 | HartlepoolvCheltenhamLeague Two · England | 2–0 | League Two · England |
| 2016-10-29 | CheltenhamvBlackpoolLeague Two · England | 2–2 | League Two · England |
| 2016-10-22 | GrimsbyvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2016-10-15 | CheltenhamvCrawley TownLeague Two · England | 2–1 | League Two · England |
| 2016-10-08 | AccringtonvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2016-10-01 | CheltenhamvLutonLeague Two · England | 1–1 | League Two · England |
| 2016-09-27 | CheltenhamvStevenageLeague Two · England | 0–0 | League Two · England |
| 2016-09-24 | YeovilvCheltenhamLeague Two · England | 4–2 | League Two · England |
| 2016-09-17 | CheltenhamvNotts CountyLeague Two · England | 2–3 | League Two · England |
| 2016-09-10 | Newport CountyvCheltenhamLeague Two · England | 2–2 | League Two · England |
| 2016-09-03 | PlymouthvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2016-08-27 | CheltenhamvCreweLeague Two · England | 2–0 | League Two · England |
| 2016-08-20 | CheltenhamvDoncasterLeague Two · England | 0–1 | League Two · England |
| 2016-08-16 | CarlislevCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2016-08-13 | MansfieldvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2016-08-06 | CheltenhamvLeyton OrientLeague Two · England | 1–1 | League Two · England |