| 1 | Tue 2 Sep | 240-2 v Plymouth ArgylePlymouth Argyle 2-0 Cheltenham Town | EFL Trophy Southern Group B |
| 2 | Sat 6 Sep | 241-0 v Accrington StanleyCheltenham Town 1-0 Accrington Stanley | Sky Bet League Two |
| 3 | Sat 13 Sep | 240-2 v Crawley TownCrawley Town 2-0 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 27 Sep | 241-7 v Grimsby TownGrimsby Town 7-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 4 Oct | 242-0 v Fleetwood TownCheltenham Town 2-0 Fleetwood Town | Sky Bet League Two |
| 6 | Sat 11 Oct | 241-1 v GillinghamGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 18 Oct | 242-0 v Newport CountyNewport County 0-2 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 25 Oct | 241-0 v WalsallCheltenham Town 1-0 Walsall | Sky Bet League Two |
| 9 | Sat 1 Nov | 241-0 v Bradford CityCheltenham Town 1-0 Bradford City | Emirates FA Cup First Round |
| 10 | Mon 10 Nov | 241-2 v Notts CountyCheltenham Town 1-2 Notts County | Sky Bet League Two |
| 11 | Sat 15 Nov | 242-3 v Tranmere RoversTranmere Rovers 3-2 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 22 Nov | 241-0 v Bristol RoversCheltenham Town 1-0 Bristol Rovers | Sky Bet League Two |
| 13 | Sat 29 Nov | 240-2 v Colchester UnitedColchester United 2-0 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 31 Jan | 241-3 v Accrington StanleyAccrington Stanley 3-1 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 14 Feb | 240-0 v BarnetBarnet 0-0 Cheltenham Town | Sky Bet League Two |
| 16 | Tue 17 Feb | 241-1 v BromleyBromley 1-1 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 21 Feb | 243-2 v Salford CityCheltenham Town 3-2 Salford City | Sky Bet League Two |
| 18 | Fri 6 Mar | 242-2 v BarrowCheltenham Town 2-2 Barrow | Sky Bet League Two |
| 19 | Tue 10 Mar | 242-2 v Fleetwood TownFleetwood Town 2-2 Cheltenham Town | Sky Bet League Two |
| 20 | Sat 14 Mar | 242-0 v Shrewsbury TownShrewsbury Town 0-2 Cheltenham Town | Sky Bet League Two |
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