| 1 | Sat 19 Jan 2019 | 0-2 v Carlisle UnitedCarlisle United 2-0 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 26 Jan 2019 | 3-2 v Macclesfield TownCheltenham Town 3-2 Macclesfield Town | Sky Bet League Two |
| 3 | Tue 5 Feb 2019 | 1-0 v Yeovil TownCheltenham Town 1-0 Yeovil Town | Sky Bet League Two |
| 4 | Sat 9 Feb 2019 | 0-3 v Colchester UnitedColchester United 3-0 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 16 Feb 2019 | 0-1 v Grimsby TownGrimsby Town 1-0 Cheltenham Town | Sky Bet League Two |
| 6 | Tue 19 Feb 2019 | 2-0 v Cambridge UnitedCheltenham Town 2-0 Cambridge United | Sky Bet League Two |
| 7 | Sat 23 Feb 2019 | 1-0 v Port ValeCheltenham Town 1-0 Port Vale | Sky Bet League Two |
| 8 | Sat 2 Mar 2019 | 2-4 v Mansfield TownMansfield Town 4-2 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 5 Mar 2019 | 1-1 v BuryCheltenham Town 1-1 Bury | Sky Bet League Two |
| 10 | Sat 9 Mar 2019 | 4-1 v Notts CountyCheltenham Town 4-1 Notts County | Sky Bet League Two |
| 11 | Fri 15 Mar 2019 | 0-1 v Newport CountyNewport County 1-0 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 23 Mar 2019 | 3-1 v Northampton TownCheltenham Town 3-1 Northampton Town | Sky Bet League Two |
| 13 | Sat 30 Mar 2019 | 3-1 v Crewe AlexandraCrewe Alexandra 1-3 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 6 Apr 2019 | 1-1 v Exeter CityCheltenham Town 1-1 Exeter City | Sky Bet League Two |
| 15 | Sat 13 Apr 2019 | 1-1 v Lincoln CityLincoln City 1-1 Cheltenham Town | Sky Bet League Two |
| 16 | Fri 19 Apr 2019 | 0-0 v Oldham AthleticCheltenham Town 0-0 Oldham Athletic | Sky Bet League Two |
| 17 | Mon 22 Apr 2019 | 0-4 v MorecambeMorecambe 4-0 Cheltenham Town | Sky Bet League Two |
| 18 | Sat 27 Apr 2019 | 3-2 v Swindon TownCheltenham Town 3-2 Swindon Town | Sky Bet League Two |
| 19 | Sat 4 May 2019 | 0-2 v StevenageStevenage 2-0 Cheltenham Town | Sky Bet League Two |
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