| 1 | Sat 8 Aug | 171-3 v Charlton AthleticCheltenham Town 1-3 Charlton Athletic | Carabao Cup First Round |
| 2 | Sat 15 Aug | 17 2-1 v Rotherham UnitedCheltenham Town 2-1 Rotherham United | Sky Bet League Two |
| 3 | Sat 29 Aug | 17 2-2 v BarnetBarnet 2-2 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 1 Sep | 17 3-2 v York CityCheltenham Town 3-2 York City | Sky Bet League Two |
| 5 | Sat 5 Sep | 172-2 v Grimsby TownCheltenham Town 2-2 Grimsby Town | Sky Bet League Two |
| 6 | Sat 12 Sep | 173-1 v Crawley TownCrawley Town 1-3 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 19 Sep | 17 1-1 v Colchester UnitedColchester United 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 13 Oct | 172-2 v Tottenham Hotspur U21Cheltenham Town 2-2 Tottenham Hotspur U21 | EFL Trophy Southern Group A |
| 9 | Sat 17 Oct | 17 1-4 v Oldham AthleticOldham Athletic 4-1 Cheltenham Town | Sky Bet League Two |
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