| 1 | Sat 2 Aug | 100-1 v Cambridge UnitedCambridge United 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 9 Aug | 100-2 v ChesterfieldCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Wed 13 Aug | 102-0 v Exeter CityCheltenham Town 2-0 Exeter City | Carabao Cup First Round |
| 4 | Sat 16 Aug | 100-5 v Milton Keynes DonsMilton Keynes Dons 5-0 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 19 Aug | 101-2 v BromleyCheltenham Town 1-2 Bromley | Sky Bet League Two |
| 6 | Sat 23 Aug | 100-1 v BarnetCheltenham Town 0-1 Barnet | Sky Bet League Two |
| 7 | Tue 26 Aug | 100-3 v Cardiff CityCardiff City 3-0 Cheltenham Town | Carabao Cup Second Round |
| 8 | Fri 29 Aug | 101-1 v Salford CitySalford City 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 2 Sep | 100-2 v Plymouth ArgylePlymouth Argyle 2-0 Cheltenham Town | EFL Trophy Southern Group B |
| 10 | Sat 6 Sep | 101-0 v Accrington StanleyCheltenham Town 1-0 Accrington Stanley | Sky Bet League Two |
| 11 | Sat 13 Sep | 100-2 v Crawley TownCrawley Town 2-0 Cheltenham Town | Sky Bet League Two |
| 12 | Thu 1 Jan | 101-4 v Crewe AlexandraCrewe Alexandra 4-1 Cheltenham Town | Sky Bet League Two |
| 13 | Sun 4 Jan | 103-0 v Crawley TownCheltenham Town 3-0 Crawley Town | Sky Bet League Two |
| 14 | Sat 17 Jan | 101-2 v Oldham AthleticOldham Athletic 2-1 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 24 Jan | 100-2 v Grimsby TownCheltenham Town 0-2 Grimsby Town | Sky Bet League Two |
| 16 | Sat 7 Feb | 102-3 v Milton Keynes DonsCheltenham Town 2-3 Milton Keynes Dons | Sky Bet League Two |
| 17 | Sat 14 Feb | 100-0 v BarnetBarnet 0-0 Cheltenham Town | Sky Bet League Two |
| 18 | Tue 17 Feb | 101-1 v BromleyBromley 1-1 Cheltenham Town | Sky Bet League Two |
| 19 | Sat 21 Feb | 103-2 v Salford CityCheltenham Town 3-2 Salford City | Sky Bet League Two |
| 20 | Fri 27 Feb | 101-1 v Harrogate TownHarrogate Town 1-1 Cheltenham Town | Sky Bet League Two |
| 21 | Fri 6 Mar | 102-2 v BarrowCheltenham Town 2-2 Barrow | Sky Bet League Two |
| 22 | Tue 10 Mar | 10 2-2 v Fleetwood TownFleetwood Town 2-2 Cheltenham Town | Sky Bet League Two |
| 23 | Sat 14 Mar | 102-0 v Shrewsbury TownShrewsbury Town 0-2 Cheltenham Town | Sky Bet League Two |
| 24 | Tue 17 Mar | 101-1 v Crewe AlexandraCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
| 25 | Sat 21 Mar | 102-5 v Notts CountyNotts County 5-2 Cheltenham Town | Sky Bet League Two |
| 26 | Fri 3 Apr | 100-1 v ChesterfieldChesterfield 1-0 Cheltenham Town | Sky Bet League Two |
| 27 | Mon 6 Apr | 101-1 v Cambridge UnitedCheltenham Town 1-1 Cambridge United | Sky Bet League Two |
| 28 | Sat 11 Apr | 104-0 v WalsallWalsall 0-4 Cheltenham Town | Sky Bet League Two |
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