| 1 | Sat 21 Jul 2018 | 0-3 v Birmingham CityCheltenham Town 0-3 Birmingham City | Friendly |
| 2 | Sat 4 Aug 2018 | 0-1 v Crawley TownCheltenham Town 0-1 Crawley Town | Sky Bet League Two |
| 3 | Sat 11 Aug 2018 | 160-1 v Tranmere RoversTranmere Rovers 1-0 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 14 Aug 2018 | 162-2 v Colchester UnitedCheltenham Town 2-2 Colchester United | Carabao Cup First Round |
| 5 | Sat 18 Aug 2018 | 160-1 v Carlisle UnitedCheltenham Town 0-1 Carlisle United | Sky Bet League Two |
| 6 | Tue 21 Aug 2018 | 161-1 v Macclesfield TownMacclesfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 7 | Tue 28 Aug 2018 | 160-1 v BrentfordBrentford 1-0 Cheltenham Town | Carabao Cup Second Round |
| 8 | Tue 23 Oct 2018 | 160-2 v Oldham AthleticOldham Athletic 2-0 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 10 Nov 2018 | 160-0 v Ebbsfleet UnitedEbbsfleet United 0-0 Cheltenham Town | Emirates FA Cup First Round |
| 10 | Tue 13 Nov 2018 | 162-0 v Coventry CityCheltenham Town 2-0 Coventry City | Checkatrade Trophy Southern Group E |
| 11 | Tue 20 Nov 2018 | 162-0 v Ebbsfleet UnitedCheltenham Town 2-0 Ebbsfleet United | Emirates FA Cup First Round Replay |
| 12 | Sat 24 Nov 2018 | 162-1 v Newport CountyCheltenham Town 2-1 Newport County | Sky Bet League Two |
| 13 | Tue 27 Nov 2018 | 161-4 v BuryBury 4-1 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 1 Dec 2018 | 161-3 v Accrington StanleyAccrington Stanley 3-1 Cheltenham Town | Emirates FA Cup Second Round |
| 15 | Tue 4 Dec 2018 | 161-1 v Newport CountyCheltenham Town 1-1 Newport County | Checkatrade Trophy Second Round |
| 16 | Sat 8 Dec 2018 | 162-1 v Grimsby TownCheltenham Town 2-1 Grimsby Town | Sky Bet League Two |
| 17 | Sat 15 Dec 2018 | 162-2 v Port ValePort Vale 2-2 Cheltenham Town | Sky Bet League Two |
| 18 | Sat 22 Dec 2018 | 160-0 v Swindon TownSwindon Town 0-0 Cheltenham Town | Sky Bet League Two |
| 19 | Wed 26 Dec 2018 | 163-1 v Milton Keynes DonsCheltenham Town 3-1 Milton Keynes Dons | Sky Bet League Two |
| 20 | Sat 29 Dec 2018 | 162-2 v Forest Green RoversCheltenham Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 21 | Tue 1 Jan 2019 | 164-1 v Yeovil TownYeovil Town 1-4 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 5 Jan 2019 | 160-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 23 | Tue 8 Jan 2019 | 16 1-1 v Oxford UnitedCheltenham Town 1-1 Oxford United | Checkatrade Trophy Second Round |
| 24 | Sat 12 Jan 2019 | 161-3 v Tranmere RoversCheltenham Town 1-3 Tranmere Rovers | Sky Bet League Two |
| 25 | Sat 19 Jan 2019 | 160-2 v Carlisle UnitedCarlisle United 2-0 Cheltenham Town | Sky Bet League Two |
| 26 | Sat 26 Jan 2019 | 163-2 v Macclesfield TownCheltenham Town 3-2 Macclesfield Town | Sky Bet League Two |
| 27 | Tue 5 Feb 2019 | 161-0 v Yeovil TownCheltenham Town 1-0 Yeovil Town | Sky Bet League Two |
| 28 | Sat 27 Apr 2019 | 163-2 v Swindon TownCheltenham Town 3-2 Swindon Town | Sky Bet League Two |
| 29 | Sat 4 May 2019 | 160-2 v StevenageStevenage 2-0 Cheltenham Town | Sky Bet League Two |
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