| 1 | Sat 10 Aug | 273-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Wed 14 Aug | 27 0-3 v Plymouth ArgylePlymouth Argyle 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug | 27 2-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 7 Sep | 271-0 v Harrogate TownCheltenham Town 1-0 Harrogate Town | Sky Bet League Two |
| 5 | Sat 14 Sep | 271-2 v Salford CitySalford City 2-1 Cheltenham Town | Sky Bet League Two |
| 6 | Sat 28 Sep | 27 0-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League Two |
| 7 | Sat 12 Oct | 272-3 v Swindon TownCheltenham Town 2-3 Swindon Town | Sky Bet League Two |
| 8 | Sat 19 Oct | 272-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 22 Oct | 27 1-1 v Bradford CityCheltenham Town 1-1 Bradford City | Sky Bet League Two |
| 10 | Sat 2 Nov | 273-1 v Rotherham UnitedRotherham United 1-3 Cheltenham Town | Emirates FA Cup First Round |
| 11 | Sat 9 Nov | 271-1 v BromleyCheltenham Town 1-1 Bromley | Sky Bet League Two |
| 12 | Sat 16 Nov | 272-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Cheltenham Town | Sky Bet League Two |
| 13 | Fri 22 Nov | 27 1-0 v Tranmere RoversCheltenham Town 1-0 Tranmere Rovers | Sky Bet League Two |
| 14 | Sat 30 Nov | 270-2 v Salford CitySalford City 2-0 Cheltenham Town | Emirates FA Cup Second Round |
| 15 | Sat 7 Dec | 272-2 v Doncaster RoversDoncaster Rovers 2-2 Cheltenham Town | Sky Bet League Two |
| 16 | Tue 10 Dec | 272-1 v Cambridge UnitedCheltenham Town 2-1 Cambridge United | EFL Trophy Second Round |
| 17 | Fri 20 Dec | 272-2 v GillinghamGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 18 | Sun 29 Dec | 27 3-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 19 | Wed 1 Jan | 270-0 v Port ValePort Vale 0-0 Cheltenham Town | Sky Bet League Two |
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