| 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 |
| 2016-04-30 | CheltenhamvLincolnNational League · England | 3–1 | National League · England |
| 2016-04-23 | MacclesfieldvCheltenhamNational League · England | 0–1 | National League · England |
| 2016-04-16 | CheltenhamvHalifaxNational League · England | 2–0 | National League · England |
| 2016-04-09 | GuiseleyvCheltenhamNational League · England | 0–2 | National League · England |
| 2016-04-01 | CheltenhamvGrimsbyNational League · England | 3–1 | National League · England |
| 2016-03-28 | WrexhamvCheltenhamNational League · England | 2–1 | National League · England |
| 2016-03-25 | CheltenhamvBoreham WoodNational League · England | 4–1 | National League · England |
| 2016-03-19 | Braintree TownvCheltenhamNational League · England | 1–0 | National League · England |
| 2016-03-12 | CheltenhamvWokingNational League · England | 4–0 | National League · England |
| 2016-03-05 | Welling UnitedvCheltenhamNational League · England | 1–1 | National League · England |
| 2016-03-01 | EastleighvCheltenhamNational League · England | 1–0 | National League · England |
| 2016-02-23 | CheltenhamvGatesheadNational League · England | 0–0 | National League · England |
| 2016-02-20 | TranmerevCheltenhamNational League · England | 0–1 | National League · England |
| 2016-02-16 | CheltenhamvKidderminsterNational League · England | 2–0 | National League · England |
| 2016-02-13 | CheltenhamvWelling UnitedNational League · England | 2–0 | National League · England |
| 2016-02-06 | BarrowvCheltenhamNational League · England | 1–2 | National League · England |
| 2016-01-30 | CheltenhamvBromleyNational League · England | 4–1 | National League · England |
| 2016-01-24 | Dover AthleticvCheltenhamNational League · England | 1–2 | National League · England |
| 2016-01-09 | Boreham WoodvCheltenhamNational League · England | 0–0 | National League · England |