| 1 | Sat 10 Aug | 53-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Wed 14 Aug | 50-3 v Plymouth ArgylePlymouth Argyle 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug | 52-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 24 Aug | 50-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Tue 3 Sep | 52-1 v Newport CountyNewport County 1-2 Cheltenham Town | EFL Trophy Southern Group H |
| 6 | Tue 1 Oct | 52-1 v Accrington StanleyCheltenham Town 2-1 Accrington Stanley | Sky Bet League Two |
| 7 | Sat 19 Oct | 52-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 3 Dec | 51-1 v Port ValeCheltenham Town 1-1 Port Vale | Sky Bet League Two |
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