| 1 | Sat 2 Aug | 20-1 v Cambridge UnitedCambridge United 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 9 Aug | 2 0-2 v ChesterfieldCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Wed 13 Aug | 22-0 v Exeter CityCheltenham Town 2-0 Exeter City | Carabao Cup First Round |
| 4 | Sat 16 Aug | 2 0-5 v Milton Keynes DonsMilton Keynes Dons 5-0 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 23 Aug | 20-1 v BarnetCheltenham Town 0-1 Barnet | Sky Bet League Two |
| 6 | Tue 26 Aug | 20-3 v Cardiff CityCardiff City 3-0 Cheltenham Town | Carabao Cup Second Round |
| 7 | Fri 29 Aug | 21-1 v Salford CitySalford City 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 2 Sep | 20-2 v Plymouth ArgylePlymouth Argyle 2-0 Cheltenham Town | EFL Trophy Southern Group B |
| 9 | Sat 6 Sep | 21-0 v Accrington StanleyCheltenham Town 1-0 Accrington Stanley | Sky Bet League Two |
| 10 | Sat 13 Sep | 20-2 v Crawley TownCrawley Town 2-0 Cheltenham Town | Sky Bet League Two |
| 11 | Sat 20 Sep | 2 0-3 v Oldham AthleticCheltenham Town 0-3 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 27 Sep | 21-7 v Grimsby TownGrimsby Town 7-1 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 4 Oct | 22-0 v Fleetwood TownCheltenham Town 2-0 Fleetwood Town | Sky Bet League Two |
| 14 | Sat 11 Oct | 21-1 v GillinghamGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 18 Oct | 22-0 v Newport CountyNewport County 0-2 Cheltenham Town | Sky Bet League Two |
| 16 | Sat 25 Oct | 21-0 v WalsallCheltenham Town 1-0 Walsall | Sky Bet League Two |
| 17 | Sat 1 Nov | 2 1-0 v Bradford CityCheltenham Town 1-0 Bradford City | Emirates FA Cup First Round |
| 18 | Sat 6 Dec | 2 6-2 v BuxtonCheltenham Town 6-2 Buxton | Emirates FA Cup Second Round |
| 19 | Tue 9 Dec | 2 1-0 v Swindon TownSwindon Town 0-1 Cheltenham Town | Sky Bet League Two |
| 20 | Sat 13 Dec | 21-1 v Harrogate TownCheltenham Town 1-1 Harrogate Town | Sky Bet League Two |
| 21 | Fri 19 Dec | 22-1 v BarrowBarrow 1-2 Cheltenham Town | Sky Bet League Two |
| 22 | Fri 26 Dec | 2 3-1 v Shrewsbury TownCheltenham Town 3-1 Shrewsbury Town | Sky Bet League Two |
| 23 | Mon 29 Dec | 20-2 v Swindon TownCheltenham Town 0-2 Swindon Town | Sky Bet League Two |
| 24 | Thu 1 Jan | 21-4 v Crewe AlexandraCrewe Alexandra 4-1 Cheltenham Town | Sky Bet League Two |
| 25 | Sun 4 Jan | 23-0 v Crawley TownCheltenham Town 3-0 Crawley Town | Sky Bet League Two |
| 26 | Sat 17 Jan | 21-2 v Oldham AthleticOldham Athletic 2-1 Cheltenham Town | Sky Bet League Two |
| 27 | Sat 24 Jan | 20-2 v Grimsby TownCheltenham Town 0-2 Grimsby Town | Sky Bet League Two |
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