| 1 | Sat 10 Aug | 183-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Wed 14 Aug | 180-3 v Plymouth ArgylePlymouth Argyle 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug | 18 2-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 24 Aug | 180-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 5 | Sat 31 Aug | 181-2 v WalsallWalsall 2-1 Cheltenham Town | Sky Bet League Two |
| 6 | Sat 21 Sep | 181-1 v ChesterfieldChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 19 Oct | 182-1 v Colchester UnitedColchester United 1-2 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 22 Oct | 181-1 v Bradford CityCheltenham Town 1-1 Bradford City | Sky Bet League Two |
| 9 | Tue 5 Nov | 181-0 v ReadingCheltenham Town 1-0 Reading | EFL Trophy Southern Group H |
| 10 | Sat 9 Nov | 181-1 v BromleyCheltenham Town 1-1 Bromley | Sky Bet League Two |
| 11 | Sat 16 Nov | 182-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Cheltenham Town | Sky Bet League Two |
| 12 | Tue 3 Dec | 18 1-1 v Port ValeCheltenham Town 1-1 Port Vale | Sky Bet League Two |
| 13 | Sat 7 Dec | 182-2 v Doncaster RoversDoncaster Rovers 2-2 Cheltenham Town | Sky Bet League Two |
| 14 | Tue 10 Dec | 182-1 v Cambridge UnitedCheltenham Town 2-1 Cambridge United | EFL Trophy Second Round |
| 15 | Sat 14 Dec | 18 2-0 v MorecambeCheltenham Town 2-0 Morecambe | Sky Bet League Two |
| 16 | Fri 20 Dec | 18 2-2 v GillinghamGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 17 | Thu 26 Dec | 182-1 v Crewe AlexandraCheltenham Town 2-1 Crewe Alexandra | Sky Bet League Two |
| 18 | Sun 29 Dec | 183-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 19 | Sat 25 Jan | 182-1 v Salford CityCheltenham Town 2-1 Salford City | Sky Bet League Two |
| 20 | Sat 1 Feb | 181-0 v ChesterfieldCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 21 | Wed 5 Feb | 182-3 v Peterborough UnitedPeterborough United 3-2 Cheltenham Town | EFL Trophy Quarter Final |
| 22 | Sat 15 Feb | 183-2 v BarrowCheltenham Town 3-2 Barrow | Sky Bet League Two |
| 23 | Tue 25 Feb | 182-2 v WalsallCheltenham Town 2-2 Walsall | Sky Bet League Two |
| 24 | Tue 4 Mar | 180-3 v Bradford CityBradford City 3-0 Cheltenham Town | Sky Bet League Two |
| 25 | Tue 11 Mar | 182-1 v AFC WimbledonAFC Wimbledon 1-2 Cheltenham Town | Sky Bet League Two |
| 26 | Sat 15 Mar | 183-3 v Swindon TownSwindon Town 3-3 Cheltenham Town | Sky Bet League Two |
| 27 | Sat 22 Mar | 180-1 v Milton Keynes DonsCheltenham Town 0-1 Milton Keynes Dons | Sky Bet League Two |
| 28 | Tue 1 Apr | 18 0-2 v MorecambeMorecambe 2-0 Cheltenham Town | Sky Bet League Two |
| 29 | Thu 10 Apr | 183-2 v Crewe AlexandraCrewe Alexandra 2-3 Cheltenham Town | Sky Bet League Two |
| 30 | Fri 18 Apr | 181-1 v GillinghamCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 31 | Mon 21 Apr | 182-1 v Notts CountyNotts County 1-2 Cheltenham Town | Sky Bet League Two |
| 32 | Sat 26 Apr | 183-2 v Carlisle UnitedCheltenham Town 3-2 Carlisle United | Sky Bet League Two |
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