| 1 | Sat 10 Aug | 123-2 v Newport CountyCheltenham Town 3-2 Newport County | Sky Bet League Two |
| 2 | Sat 17 Aug | 12 2-3 v Grimsby TownGrimsby Town 3-2 Cheltenham Town | Sky Bet League Two |
| 3 | Sat 24 Aug | 120-1 v AFC WimbledonCheltenham Town 0-1 AFC Wimbledon | Sky Bet League Two |
| 4 | Sat 31 Aug | 121-2 v WalsallWalsall 2-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 7 Sep | 121-0 v Harrogate TownCheltenham Town 1-0 Harrogate Town | Sky Bet League Two |
| 6 | Sat 14 Sep | 121-2 v Salford CitySalford City 2-1 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 28 Sep | 120-2 v Fleetwood TownCheltenham Town 0-2 Fleetwood Town | Sky Bet League Two |
| 8 | Tue 1 Oct | 122-1 v Accrington StanleyCheltenham Town 2-1 Accrington Stanley | Sky Bet League Two |
| 9 | Sat 5 Oct | 121-2 v BarrowBarrow 2-1 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 12 Oct | 122-3 v Swindon TownCheltenham Town 2-3 Swindon Town | Sky Bet League Two |
| 11 | Tue 22 Oct | 121-1 v Bradford CityCheltenham Town 1-1 Bradford City | Sky Bet League Two |
| 12 | Tue 5 Nov | 121-0 v ReadingCheltenham Town 1-0 Reading | EFL Trophy Southern Group H |
| 13 | Sat 9 Nov | 121-1 v BromleyCheltenham Town 1-1 Bromley | Sky Bet League Two |
| 14 | Sat 16 Nov | 122-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 30 Nov | 120-2 v Salford CitySalford City 2-0 Cheltenham Town | Emirates FA Cup Second Round |
| 16 | Tue 10 Dec | 122-1 v Cambridge UnitedCheltenham Town 2-1 Cambridge United | EFL Trophy Second Round |
| 17 | Sat 14 Dec | 122-0 v MorecambeCheltenham Town 2-0 Morecambe | Sky Bet League Two |
| 18 | Thu 26 Dec | 12 2-1 v Crewe AlexandraCheltenham Town 2-1 Crewe Alexandra | Sky Bet League Two |
| 19 | Sun 29 Dec | 123-5 v Notts CountyCheltenham Town 3-5 Notts County | Sky Bet League Two |
| 20 | Wed 1 Jan | 120-0 v Port ValePort Vale 0-0 Cheltenham Town | Sky Bet League Two |
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