| 1 | Sat 3 Aug 2019 | 32 0-1 v Leyton OrientLeyton Orient 1-0 Cheltenham Town | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 320-3 v Bristol RoversBristol Rovers 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 320-0 v MorecambeMorecambe 0-0 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 322-0 v Carlisle UnitedCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 322-2 v Swindon TownCheltenham Town 2-2 Swindon Town | Sky Bet League Two |
| 6 | Sat 7 Sep 2019 | 324-2 v StevenageCheltenham Town 4-2 Stevenage | Sky Bet League Two |
| 7 | Sat 14 Sep 2019 | 322-0 v Salford CitySalford City 0-2 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 17 Sep 2019 | 323-2 v Bradford CityCheltenham Town 3-2 Bradford City | Sky Bet League Two |
| 9 | Sat 21 Sep 2019 | 32 2-0 v Plymouth ArgylePlymouth Argyle 0-2 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 28 Sep 2019 | 32 1-1 v Crewe AlexandraCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
| 11 | Sat 19 Oct 2019 | 322-1 v WalsallWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 12 | Tue 22 Oct 2019 | 323-0 v Macclesfield TownCheltenham Town 3-0 Macclesfield Town | Sky Bet League Two |
| 13 | Sat 2 Nov 2019 | 321-2 v Forest Green RoversCheltenham Town 1-2 Forest Green Rovers | Sky Bet League Two |
| 14 | Sat 9 Nov 2019 | 321-1 v Swindon TownCheltenham Town 1-1 Swindon Town | Emirates FA Cup First Round |
| 15 | Sat 16 Nov 2019 | 32 0-0 v Exeter CityExeter City 0-0 Cheltenham Town | Sky Bet League Two |
| 16 | Tue 28 Jan 2020 | 321-1 v Bradford CityBradford City 1-1 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 1 Feb 2020 | 32 2-1 v MorecambeCheltenham Town 2-1 Morecambe | Sky Bet League Two |
| 18 | Sat 8 Feb 2020 | 320-1 v Scunthorpe UnitedScunthorpe United 1-0 Cheltenham Town | Sky Bet League Two |
| 19 | Tue 11 Feb 2020 | 321-0 v Carlisle UnitedCarlisle United 0-1 Cheltenham Town | Sky Bet League Two |
| 20 | Sat 15 Feb 2020 | 322-1 v Leyton OrientCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 21 | Sat 22 Feb 2020 | 321-0 v Mansfield TownCheltenham Town 1-0 Mansfield Town | Sky Bet League Two |
| 22 | Tue 25 Feb 2020 | 32 2-1 v Northampton TownCheltenham Town 2-1 Northampton Town | Sky Bet League Two |
| 23 | Sat 29 Feb 2020 | 322-0 v Colchester UnitedColchester United 0-2 Cheltenham Town | Sky Bet League Two |
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