| 1 | Sat 3 Aug 2019 | 150-1 v Leyton OrientLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 9 Nov 2019 | 15 1-1 v Swindon TownCheltenham Town 1-1 Swindon Town | Emirates FA Cup First Round |
| 3 | Tue 12 Nov 2019 | 154-7 v Newport CountyCheltenham Town 4-7 Newport County | Leasing.com Trophy Southern Group E |
| 4 | Tue 26 Nov 2019 | 150-0 v Grimsby TownGrimsby Town 0-0 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 30 Nov 2019 | 151-3 v Port ValeCheltenham Town 1-3 Port Vale | Emirates FA Cup Second Round |
| 6 | Sat 7 Dec 2019 | 15 3-0 v Mansfield TownMansfield Town 0-3 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 14 Dec 2019 | 151-1 v Cambridge UnitedCheltenham Town 1-1 Cambridge United | Sky Bet League Two |
| 8 | Thu 26 Dec 2019 | 150-1 v Plymouth ArgyleCheltenham Town 0-1 Plymouth Argyle | Sky Bet League Two |
| 9 | Wed 1 Jan 2020 | 151-1 v Newport CountyNewport County 1-1 Cheltenham Town | Sky Bet League Two |
| 10 | Tue 28 Jan 2020 | 151-1 v Bradford CityBradford City 1-1 Cheltenham Town | Sky Bet League Two |
| 11 | Tue 11 Feb 2020 | 151-0 v Carlisle UnitedCarlisle United 0-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 15 Feb 2020 | 152-1 v Leyton OrientCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 13 | Sat 22 Feb 2020 | 151-0 v Mansfield TownCheltenham Town 1-0 Mansfield Town | Sky Bet League Two |
| 14 | Tue 25 Feb 2020 | 15 2-1 v Northampton TownCheltenham Town 2-1 Northampton Town | Sky Bet League Two |
| 15 | Sat 29 Feb 2020 | 152-0 v Colchester UnitedColchester United 0-2 Cheltenham Town | Sky Bet League Two |
| 16 | Sat 7 Mar 2020 | 150-0 v Port ValeCheltenham Town 0-0 Port Vale | Sky Bet League Two |
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