| 1 | Sat 3 Aug 2019 | 0-1 v Leyton OrientLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 4-1 v Scunthorpe UnitedCheltenham Town 4-1 Scunthorpe United | Sky Bet League Two |
| 3 | Tue 20 Aug 2019 | 2-0 v Carlisle UnitedCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
| 4 | Sat 24 Aug 2019 | 2-2 v Swindon TownCheltenham Town 2-2 Swindon Town | Sky Bet League Two |
| 5 | Sat 31 Aug 2019 | 0-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 6 | Tue 3 Sep 2019 | 0-1 v Exeter CityExeter City 1-0 Cheltenham Town | Leasing.com Trophy Southern Group E |
| 7 | Sun 29 Dec 2019 | 1-1 v Northampton TownNorthampton Town 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Wed 1 Jan 2020 | 1-1 v Newport CountyNewport County 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 4 Jan 2020 | 3-0 v Oldham AthleticCheltenham Town 3-0 Oldham Athletic | Sky Bet League Two |
| 10 | Sat 11 Jan 2020 | 3-1 v WalsallCheltenham Town 3-1 Walsall | Sky Bet League Two |
| 11 | Sat 18 Jan 2020 | 0-1 v Crewe AlexandraCrewe Alexandra 1-0 Cheltenham Town | Sky Bet League Two |
| 12 | Tue 28 Jan 2020 | 1-1 v Bradford CityBradford City 1-1 Cheltenham Town | Sky Bet League Two |
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