| 1 | Sat 3 Aug 2019 | 0-1 v Leyton OrientLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 31 Aug 2019 | 0-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 3 | Sat 19 Oct 2019 | 2-1 v WalsallWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 22 Oct 2019 | 3-0 v Macclesfield TownCheltenham Town 3-0 Macclesfield Town | Sky Bet League Two |
| 5 | Sat 2 Nov 2019 | 1-2 v Forest Green RoversCheltenham Town 1-2 Forest Green Rovers | Sky Bet League Two |
| 6 | Sat 9 Nov 2019 | 1-1 v Swindon TownCheltenham Town 1-1 Swindon Town | Emirates FA Cup First Round |
| 7 | Tue 12 Nov 2019 | 4-7 v Newport CountyCheltenham Town 4-7 Newport County | Leasing.com Trophy Southern Group E |
| 8 | Sat 30 Nov 2019 | 1-3 v Port ValeCheltenham Town 1-3 Port Vale | Emirates FA Cup Second Round |
| 9 | Sun 29 Dec 2019 | 1-1 v Northampton TownNorthampton Town 1-1 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 1 Feb 2020 | 2-1 v MorecambeCheltenham Town 2-1 Morecambe | Sky Bet League Two |
| 11 | Tue 11 Feb 2020 | 1-0 v Carlisle UnitedCarlisle United 0-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 29 Feb 2020 | 2-0 v Colchester UnitedColchester United 0-2 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 7 Mar 2020 | 0-0 v Port ValeCheltenham Town 0-0 Port Vale | Sky Bet League Two |
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