| 1 | 10/8/2019 | 4-1 v Scunthorpe UnitedCheltenham Town 4-1 Scunthorpe United | Sky Bet League Two |
| 2 | 13/8/2019 | 0-3 v Bristol RoversBristol Rovers 3-0 Cheltenham Town | Carabao Cup First Round |
| 3 | 17/8/2019 | 0-0 v MorecambeMorecambe 0-0 Cheltenham Town | Sky Bet League Two |
| 4 | 20/8/2019 | 2-0 v Carlisle UnitedCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
| 5 | 24/8/2019 | 2-2 v Swindon TownCheltenham Town 2-2 Swindon Town | Sky Bet League Two |
| 6 | 31/8/2019 | 0-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 7 | 3/9/2019 | 0-1 v Exeter CityExeter City 1-0 Cheltenham Town | Checkatrade Trophy Southern Group E |
| 8 | 7/9/2019 | 4-2 v StevenageCheltenham Town 4-2 Stevenage | Sky Bet League Two |
| 9 | 14/9/2019 | 2-0 v Salford CitySalford City 0-2 Cheltenham Town | Sky Bet League Two |
| 10 | 17/9/2019 | 3-2 v Bradford CityCheltenham Town 3-2 Bradford City | Sky Bet League Two |
| 11 | 21/9/2019 | 2-0 v Plymouth ArgylePlymouth Argyle 0-2 Cheltenham Town | Sky Bet League Two |
| 12 | 28/9/2019 | 1-1 v Crewe AlexandraCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
| 13 | 5/10/2019 | 1-1 v Oldham AthleticOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
| 14 | 19/10/2019 | 2-1 v WalsallWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 15 | 22/10/2019 | 3-0 v Macclesfield TownCheltenham Town 3-0 Macclesfield Town | Sky Bet League Two |
| 16 | 2/11/2019 | 1-2 v Forest Green RoversCheltenham Town 1-2 Forest Green Rovers | Sky Bet League Two |
| 17 | 12/11/2019 | 4-7 v Newport CountyCheltenham Town 4-7 Newport County | Checkatrade Trophy Southern Group E |
| 18 | 19/11/2019 | 1-0 v Swindon TownSwindon Town 0-1 Cheltenham Town | Emirates FA Cup First Round Replay |
| 19 | 23/11/2019 | 1-1 v Colchester UnitedCheltenham Town 1-1 Colchester United | Sky Bet League Two |
| 20 | 26/11/2019 | 0-0 v Grimsby TownGrimsby Town 0-0 Cheltenham Town | Sky Bet League Two |
| 21 | 30/11/2019 | 1-3 v Port ValeCheltenham Town 1-3 Port Vale | Emirates FA Cup Second Round |
| 22 | 7/12/2019 | 3-0 v Mansfield TownMansfield Town 0-3 Cheltenham Town | Sky Bet League Two |
