| 1 | Sat 8 Aug | 31-3 v Charlton AthleticCheltenham Town 1-3 Charlton Athletic | Carabao Cup First Round |
| 2 | Sat 15 Aug | 3 2-1 v Rotherham UnitedCheltenham Town 2-1 Rotherham United | Sky Bet League Two |
| 3 | Sat 22 Aug | 31-2 v Swindon TownSwindon Town 2-1 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 29 Aug | 3 2-2 v BarnetBarnet 2-2 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 1 Sep | 33-2 v York CityCheltenham Town 3-2 York City | Sky Bet League Two |
| 6 | Sat 5 Sep | 3 2-2 v Grimsby TownCheltenham Town 2-2 Grimsby Town | Sky Bet League Two |
| 7 | Sat 12 Sep | 33-1 v Crawley TownCrawley Town 1-3 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 19 Sep | 3 1-1 v Colchester UnitedColchester United 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 26 Sep | 32-1 v ChesterfieldCheltenham Town 2-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 3 Oct | 30-2 v Accrington StanleyAccrington Stanley 2-0 Cheltenham Town | Sky Bet League Two |
| 11 | Sat 10 Oct | 3 0-2 v Salford CityCheltenham Town 0-2 Salford City | Sky Bet League Two |
| 12 | Tue 13 Oct | 32-2 v Tottenham Hotspur U21Cheltenham Town 2-2 Tottenham Hotspur U21 | EFL Trophy Southern Group A |
| 13 | Tue 20 Oct | 3 4-2 v Fleetwood TownCheltenham Town 4-2 Fleetwood Town | Sky Bet League Two |
| 14 | Sat 24 Oct | 31-0 v Newport CountyCheltenham Town 1-0 Newport County | Sky Bet League Two |
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