| 1 | Sat 5 Aug | 14 0-1 v Shrewsbury TownShrewsbury Town 1-0 Cheltenham Town | Sky Bet League One |
| 2 | Tue 15 Aug | 140-1 v ReadingReading 1-0 Cheltenham Town | Sky Bet League One |
| 3 | Sat 19 Aug | 14 0-0 v PortsmouthPortsmouth 0-0 Cheltenham Town | Sky Bet League One |
| 4 | Sat 26 Aug | 140-1 v Northampton TownCheltenham Town 0-1 Northampton Town | Sky Bet League One |
| 5 | Sat 2 Sep | 140-2 v BarnsleyCheltenham Town 0-2 Barnsley | Sky Bet League One |
| 6 | Sat 30 Sep | 140-2 v Lincoln CityLincoln City 2-0 Cheltenham Town | Sky Bet League One |
| 7 | Tue 3 Oct | 140-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League One |
| 8 | Sat 7 Oct | 141-1 v Derby CountyCheltenham Town 1-1 Derby County | Sky Bet League One |
| 9 | Tue 10 Oct | 140-2 v Newport CountyCheltenham Town 0-2 Newport County | EFL Trophy |
| 10 | Sat 21 Oct | 141-0 v Cambridge UnitedCheltenham Town 1-0 Cambridge United | Sky Bet League One |
| 11 | Tue 24 Oct | 142-3 v BlackpoolBlackpool 3-2 Cheltenham Town | Sky Bet League One |
| 12 | Sat 28 Oct | 142-1 v Port ValePort Vale 1-2 Cheltenham Town | Sky Bet League One |
| 13 | Sat 4 Nov | 14 1-5 v AFC WimbledonAFC Wimbledon 5-1 Cheltenham Town | Emirates FA Cup First Round |
| 14 | Sat 11 Nov | 141-1 v Wigan AthleticCheltenham Town 1-1 Wigan Athletic | Sky Bet League One |
| 15 | Sat 16 Dec | 141-2 v Leyton OrientCheltenham Town 1-2 Leyton Orient | Sky Bet League One |
| 16 | Tue 26 Dec | 14 2-0 v Shrewsbury TownCheltenham Town 2-0 Shrewsbury Town | Sky Bet League One |
| 17 | Fri 29 Dec | 142-2 v ReadingCheltenham Town 2-2 Reading | Sky Bet League One |
| 18 | Mon 1 Jan | 140-1 v Northampton TownNorthampton Town 1-0 Cheltenham Town | Sky Bet League One |
| 19 | Sat 6 Jan | 142-1 v PortsmouthCheltenham Town 2-1 Portsmouth | Sky Bet League One |
| 20 | Sat 27 Jan | 141-2 v Derby CountyDerby County 2-1 Cheltenham Town | Sky Bet League One |
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