| 1 | Sat 10 Aug | 143-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Wed 14 Aug | 140-3 v Plymouth ArgylePlymouth Argyle 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug | 142-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 24 Aug | 140-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Sat 31 Aug | 141-2 v WalsallWalsall 2-1 Cheltenham Town | Sky Bet League Two |
| 6 | Tue 3 Sep | 142-1 v Newport CountyNewport County 1-2 Cheltenham Town | EFL Trophy Southern Group H |
| 7 | Sat 7 Sep | 141-0 v Harrogate TownCheltenham Town 1-0 Harrogate Town | Sky Bet League Two |
| 8 | Sat 14 Sep | 141-2 v Salford CitySalford City 2-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 21 Sep | 141-1 v ChesterfieldChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 28 Sep | 140-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League Two |
| 11 | Sat 5 Oct | 141-2 v BarrowBarrow 2-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 12 Oct | 142-3 v Swindon TownCheltenham Town 2-3 Swindon Town | Sky Bet League Two |
| 13 | Sat 19 Oct | 142-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 14 | Tue 5 Nov | 141-0 v ReadingCheltenham Town 1-0 Reading | EFL Trophy Southern Group H |
| 15 | Sat 16 Nov | 142-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Cheltenham Town | Sky Bet League Two |
| 16 | Sat 30 Nov | 140-2 v Salford CitySalford City 2-0 Cheltenham Town | Emirates FA Cup Second Round |
| 17 | Tue 10 Dec | 142-1 v Cambridge UnitedCheltenham Town 2-1 Cambridge United | EFL Trophy Second Round |
| 18 | Sat 14 Dec | 142-0 v MorecambeCheltenham Town 2-0 Morecambe | Sky Bet League Two |
| 19 | Fri 20 Dec | 142-2 v GillinghamGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 20 | Sun 29 Dec | 143-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 21 | Wed 1 Jan | 140-0 v Port ValePort Vale 0-0 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 8 Feb | 140-2 v Fleetwood TownFleetwood Town 2-0 Cheltenham Town | Sky Bet League Two |
| 23 | Sat 22 Feb | 143-0 v Newport CountyNewport County 0-3 Cheltenham Town | Sky Bet League Two |
| 24 | Tue 25 Feb | 142-2 v WalsallCheltenham Town 2-2 Walsall | Sky Bet League Two |
| 25 | Sat 1 Mar | 141-1 v Grimsby TownCheltenham Town 1-1 Grimsby Town | Sky Bet League Two |
| 26 | Tue 4 Mar | 14 0-3 v Bradford CityBradford City 3-0 Cheltenham Town | Sky Bet League Two |
| 27 | Sat 22 Mar | 140-1 v Milton Keynes DonsCheltenham Town 0-1 Milton Keynes Dons | Sky Bet League Two |
| 28 | Tue 1 Apr | 140-2 v MorecambeMorecambe 2-0 Cheltenham Town | Sky Bet League Two |
| 29 | Sat 5 Apr | 140-2 v Doncaster RoversCheltenham Town 0-2 Doncaster Rovers | Sky Bet League Two |
| 30 | Thu 10 Apr | 143-2 v Crewe AlexandraCrewe Alexandra 2-3 Cheltenham Town | Sky Bet League Two |
| 31 | Fri 18 Apr | 141-1 v GillinghamCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 32 | Mon 21 Apr | 142-1 v Notts CountyNotts County 1-2 Cheltenham Town | Sky Bet League Two |
| 33 | Sat 26 Apr | 143-2 v Carlisle UnitedCheltenham Town 3-2 Carlisle United | Sky Bet League Two |
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