| 1 | Sat 2 Aug | 12 0-1 v Cambridge UnitedCambridge United 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 9 Aug | 120-2 v ChesterfieldCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Wed 13 Aug | 122-0 v Exeter CityCheltenham Town 2-0 Exeter City | Carabao Cup First Round |
| 4 | Sat 16 Aug | 120-5 v Milton Keynes DonsMilton Keynes Dons 5-0 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 19 Aug | 121-2 v BromleyCheltenham Town 1-2 Bromley | Sky Bet League Two |
| 6 | Sat 23 Aug | 120-1 v BarnetCheltenham Town 0-1 Barnet | Sky Bet League Two |
| 7 | Tue 26 Aug | 120-3 v Cardiff CityCardiff City 3-0 Cheltenham Town | Carabao Cup Second Round |
| 8 | Sat 6 Sep | 121-0 v Accrington StanleyCheltenham Town 1-0 Accrington Stanley | Sky Bet League Two |
| 9 | Sat 13 Sep | 120-2 v Crawley TownCrawley Town 2-0 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 20 Sep | 120-3 v Oldham AthleticCheltenham Town 0-3 Oldham Athletic | Sky Bet League Two |
| 11 | Sat 27 Sep | 121-7 v Grimsby TownGrimsby Town 7-1 Cheltenham Town | Sky Bet League Two |
| 12 | Tue 7 Oct | 120-1 v Bristol RoversCheltenham Town 0-1 Bristol Rovers | EFL Trophy Southern Group B |
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