| 1 | Sat 24 Aug | 250-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 2 | Sat 31 Aug | 25 1-2 v WalsallWalsall 2-1 Cheltenham Town | Sky Bet League Two |
| 3 | Sat 7 Sep | 251-0 v Harrogate TownCheltenham Town 1-0 Harrogate Town | Sky Bet League Two |
| 4 | Sat 14 Sep | 251-2 v Salford CitySalford City 2-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 21 Sep | 25 1-1 v ChesterfieldChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 6 | Sat 28 Sep | 250-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League Two |
| 7 | Tue 1 Oct | 252-1 v Accrington StanleyCheltenham Town 2-1 Accrington Stanley | Sky Bet League Two |
| 8 | Sat 5 Oct | 251-2 v BarrowBarrow 2-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 12 Oct | 252-3 v Swindon TownCheltenham Town 2-3 Swindon Town | Sky Bet League Two |
| 10 | Sat 19 Oct | 252-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 11 | Sat 2 Nov | 253-1 v Rotherham UnitedRotherham United 1-3 Cheltenham Town | Emirates FA Cup First Round |
| 12 | Sat 9 Nov | 251-1 v BromleyCheltenham Town 1-1 Bromley | Sky Bet League Two |
| 13 | Fri 22 Nov | 251-0 v Tranmere RoversCheltenham Town 1-0 Tranmere Rovers | Sky Bet League Two |
| 14 | Sat 30 Nov | 25 0-2 v Salford CitySalford City 2-0 Cheltenham Town | Emirates FA Cup Second Round |
| 15 | Tue 3 Dec | 251-1 v Port ValeCheltenham Town 1-1 Port Vale | Sky Bet League Two |
| 16 | Sat 7 Dec | 252-2 v Doncaster RoversDoncaster Rovers 2-2 Cheltenham Town | Sky Bet League Two |
| 17 | Tue 10 Dec | 252-1 v Cambridge UnitedCheltenham Town 2-1 Cambridge United | EFL Trophy Second Round |
| 18 | Sat 14 Dec | 252-0 v MorecambeCheltenham Town 2-0 Morecambe | Sky Bet League Two |
| 19 | Fri 20 Dec | 252-2 v GillinghamGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 20 | Thu 26 Dec | 252-1 v Crewe AlexandraCheltenham Town 2-1 Crewe Alexandra | Sky Bet League Two |
| 21 | Sun 29 Dec | 253-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 22 | Wed 1 Jan | 250-0 v Port ValePort Vale 0-0 Cheltenham Town | Sky Bet League Two |
| 23 | Sat 25 Jan | 252-1 v Salford CityCheltenham Town 2-1 Salford City | Sky Bet League Two |
| 24 | Tue 28 Jan | 250-0 v Accrington StanleyAccrington Stanley 0-0 Cheltenham Town | Sky Bet League Two |
| 25 | Sat 1 Feb | 251-0 v ChesterfieldCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 26 | Wed 5 Feb | 25 2-3 v Peterborough UnitedPeterborough United 3-2 Cheltenham Town | EFL Trophy Quarter Final |
| 27 | Sat 8 Feb | 25 0-2 v Fleetwood TownFleetwood Town 2-0 Cheltenham Town | Sky Bet League Two |
| 28 | Sat 15 Feb | 253-2 v BarrowCheltenham Town 3-2 Barrow | Sky Bet League Two |
| 29 | Sat 22 Feb | 253-0 v Newport CountyNewport County 0-3 Cheltenham Town | Sky Bet League Two |
| 30 | Tue 25 Feb | 252-2 v WalsallCheltenham Town 2-2 Walsall | Sky Bet League Two |
| 31 | Sat 1 Mar | 251-1 v Grimsby TownCheltenham Town 1-1 Grimsby Town | Sky Bet League Two |
| 32 | Sat 8 Mar | 250-1 v Colchester UnitedCheltenham Town 0-1 Colchester United | Sky Bet League Two |
| 33 | Tue 11 Mar | 252-1 v AFC WimbledonAFC Wimbledon 1-2 Cheltenham Town | Sky Bet League Two |
| 34 | Sat 15 Mar | 25 3-3 v Swindon TownSwindon Town 3-3 Cheltenham Town | Sky Bet League Two |
| 35 | Sat 22 Mar | 250-1 v Milton Keynes DonsCheltenham Town 0-1 Milton Keynes Dons | Sky Bet League Two |
| 36 | Fri 28 Mar | 250-2 v Tranmere RoversTranmere Rovers 2-0 Cheltenham Town | Sky Bet League Two |
| 37 | Tue 1 Apr | 250-2 v MorecambeMorecambe 2-0 Cheltenham Town | Sky Bet League Two |
| 38 | Sat 5 Apr | 250-2 v Doncaster RoversCheltenham Town 0-2 Doncaster Rovers | Sky Bet League Two |
| 39 | Thu 10 Apr | 253-2 v Crewe AlexandraCrewe Alexandra 2-3 Cheltenham Town | Sky Bet League Two |
| 40 | Fri 18 Apr | 251-1 v GillinghamCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 41 | Mon 21 Apr | 252-1 v Notts CountyNotts County 1-2 Cheltenham Town | Sky Bet League Two |
| 42 | Sat 26 Apr | 253-2 v Carlisle UnitedCheltenham Town 3-2 Carlisle United | Sky Bet League Two |
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