| 2021-05-08 | CheltenhamvHarrogateLeague Two · England | 4–1 | League Two · England |
| 2021-05-01 | Newport CountyvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2021-04-27 | CheltenhamvCarlisleLeague Two · England | 1–1 | League Two · England |
| 2021-04-24 | CheltenhamvColchesterLeague Two · England | 1–0 | League Two · England |
| 2021-04-20 | StevenagevCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2021-04-16 | Crawley TownvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2021-04-10 | CheltenhamvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 2021-04-05 | GrimsbyvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2021-04-02 | CheltenhamvTranmereLeague Two · England | 4–0 | League Two · England |
| 2021-03-27 | MorecambevCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2021-03-20 | CheltenhamvSalfordLeague Two · England | 2–0 | League Two · England |
| 2021-03-16 | CheltenhamvBarrowLeague Two · England | 0–2 | League Two · England |
| 2021-03-13 | ExetervCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2021-03-09 | MansfieldvCheltenhamLeague Two · England | 3–1 | League Two · England |
| 2021-03-06 | CheltenhamvPort ValeLeague Two · England | 3–2 | League Two · England |
| 2021-03-02 | CheltenhamvSouthendLeague Two · England | 1–0 | League Two · England |
| 2021-02-27 | ScunthorpevCheltenhamLeague Two · England | 0–2 | League Two · England |
| 2021-02-23 | CambridgevCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2021-02-20 | CheltenhamvBradfordLeague Two · England | 0–2 | League Two · England |
| 2021-02-16 | WalsallvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 2021-02-09 | HarrogatevCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2021-01-30 | Forest GreenvCheltenhamLeague Two · England | 0–0 | League Two · England |
| 2021-01-26 | CheltenhamvOldhamLeague Two · England | 2–0 | League Two · England |
| 2021-01-19 | CheltenhamvNewport CountyLeague Two · England | 1–1 | League Two · England |
| 2021-01-16 | BoltonvCheltenhamLeague Two · England | 1–1 | League Two · England |