| 1 | Sat 10 Aug | 163-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Wed 14 Aug | 160-3 v Plymouth ArgylePlymouth Argyle 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug | 162-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 24 Aug | 160-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Sat 31 Aug | 161-2 v WalsallWalsall 2-1 Cheltenham Town | Sky Bet League Two |
| 6 | Tue 3 Sep | 162-1 v Newport CountyNewport County 1-2 Cheltenham Town | EFL Trophy Southern Group H |
| 7 | Sat 14 Sep | 161-2 v Salford CitySalford City 2-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 21 Sep | 161-1 v ChesterfieldChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 28 Sep | 160-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League Two |
| 10 | Tue 1 Oct | 16 2-1 v Accrington StanleyCheltenham Town 2-1 Accrington Stanley | Sky Bet League Two |
| 11 | Sat 5 Oct | 161-2 v BarrowBarrow 2-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 19 Oct | 162-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 13 | Tue 22 Oct | 16 1-1 v Bradford CityCheltenham Town 1-1 Bradford City | Sky Bet League Two |
| 14 | Sat 2 Nov | 163-1 v Rotherham UnitedRotherham United 1-3 Cheltenham Town | Emirates FA Cup First Round |
| 15 | Tue 5 Nov | 16 1-0 v ReadingCheltenham Town 1-0 Reading | EFL Trophy Southern Group H |
| 16 | Sat 9 Nov | 161-1 v BromleyCheltenham Town 1-1 Bromley | Sky Bet League Two |
| 17 | Sat 16 Nov | 162-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Cheltenham Town | Sky Bet League Two |
| 18 | Fri 22 Nov | 161-0 v Tranmere RoversCheltenham Town 1-0 Tranmere Rovers | Sky Bet League Two |
| 19 | Sat 30 Nov | 160-2 v Salford CitySalford City 2-0 Cheltenham Town | Emirates FA Cup Second Round |
| 20 | Tue 3 Dec | 161-1 v Port ValeCheltenham Town 1-1 Port Vale | Sky Bet League Two |
| 21 | Sat 7 Dec | 162-2 v Doncaster RoversDoncaster Rovers 2-2 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 14 Dec | 162-0 v MorecambeCheltenham Town 2-0 Morecambe | Sky Bet League Two |
| 23 | Fri 20 Dec | 162-2 v GillinghamGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 24 | Thu 26 Dec | 162-1 v Crewe AlexandraCheltenham Town 2-1 Crewe Alexandra | Sky Bet League Two |
| 25 | Sun 29 Dec | 163-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 26 | Wed 1 Jan | 160-0 v Port ValePort Vale 0-0 Cheltenham Town | Sky Bet League Two |
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