| 1 | Sat 2 Aug | 10-1 v Cambridge UnitedCambridge United 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 9 Aug | 10-2 v ChesterfieldCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Wed 13 Aug | 12-0 v Exeter CityCheltenham Town 2-0 Exeter City | Carabao Cup First Round |
| 4 | Sat 16 Aug | 10-5 v Milton Keynes DonsMilton Keynes Dons 5-0 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 19 Aug | 11-2 v BromleyCheltenham Town 1-2 Bromley | Sky Bet League Two |
| 6 | Sat 23 Aug | 10-1 v BarnetCheltenham Town 0-1 Barnet | Sky Bet League Two |
| 7 | Tue 26 Aug | 10-3 v Cardiff CityCardiff City 3-0 Cheltenham Town | Carabao Cup Second Round |
| 8 | Fri 29 Aug | 11-1 v Salford CitySalford City 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 6 Sep | 11-0 v Accrington StanleyCheltenham Town 1-0 Accrington Stanley | Sky Bet League Two |
| 10 | Sat 13 Sep | 10-2 v Crawley TownCrawley Town 2-0 Cheltenham Town | Sky Bet League Two |
| 11 | Sat 20 Sep | 10-3 v Oldham AthleticCheltenham Town 0-3 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 27 Sep | 11-7 v Grimsby TownGrimsby Town 7-1 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 4 Oct | 12-0 v Fleetwood TownCheltenham Town 2-0 Fleetwood Town | Sky Bet League Two |
| 14 | Sat 11 Oct | 11-1 v GillinghamGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 18 Oct | 12-0 v Newport CountyNewport County 0-2 Cheltenham Town | Sky Bet League Two |
| 16 | Sat 25 Oct | 11-0 v WalsallCheltenham Town 1-0 Walsall | Sky Bet League Two |
| 17 | Sat 1 Nov | 11-0 v Bradford CityCheltenham Town 1-0 Bradford City | Emirates FA Cup First Round |
| 18 | Mon 10 Nov | 11-2 v Notts CountyCheltenham Town 1-2 Notts County | Sky Bet League Two |
| 19 | Sat 15 Nov | 12-3 v Tranmere RoversTranmere Rovers 3-2 Cheltenham Town | Sky Bet League Two |
| 20 | Sat 22 Nov | 11-0 v Bristol RoversCheltenham Town 1-0 Bristol Rovers | Sky Bet League Two |
| 21 | Sat 29 Nov | 10-2 v Colchester UnitedColchester United 2-0 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 6 Dec | 16-2 v BuxtonCheltenham Town 6-2 Buxton | Emirates FA Cup Second Round |
| 23 | Tue 9 Dec | 1 1-0 v Swindon TownSwindon Town 0-1 Cheltenham Town | Sky Bet League Two |
| 24 | Sat 13 Dec | 11-1 v Harrogate TownCheltenham Town 1-1 Harrogate Town | Sky Bet League Two |
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