| 1 | Fri 13 Jul 2018 | 244-0 v Cirencester TownCirencester Town 0-4 Cheltenham Town | Friendly |
| 2 | Sat 21 Jul 2018 | 10-3 v Birmingham CityCheltenham Town 0-3 Birmingham City | Friendly |
| 3 | Sat 4 Aug 2018 | 1 0-1 v Crawley TownCheltenham Town 0-1 Crawley Town | Sky Bet League Two |
| 4 | Sat 11 Aug 2018 | 10-1 v Tranmere RoversTranmere Rovers 1-0 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 14 Aug 2018 | 12-2 v Colchester UnitedCheltenham Town 2-2 Colchester United | Carabao Cup First Round |
| 6 | Sat 18 Aug 2018 | 10-1 v Carlisle UnitedCheltenham Town 0-1 Carlisle United | Sky Bet League Two |
| 7 | Tue 21 Aug 2018 | 11-1 v Macclesfield TownMacclesfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 25 Aug 2018 | 11-0 v Cambridge UnitedCambridge United 0-1 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 28 Aug 2018 | 10-1 v BrentfordBrentford 1-0 Cheltenham Town | Carabao Cup Second Round |
| 10 | Sat 1 Sep 2018 | 11-3 v Colchester UnitedCheltenham Town 1-3 Colchester United | Sky Bet League Two |
| 11 | Sat 8 Sep 2018 | 1 3-1 v Northampton TownNorthampton Town 1-3 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 15 Sep 2018 | 10-0 v Crewe AlexandraCheltenham Town 0-0 Crewe Alexandra | Sky Bet League Two |
| 13 | Sat 22 Sep 2018 | 11-3 v Exeter CityExeter City 3-1 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 29 Sep 2018 | 10-2 v Lincoln CityCheltenham Town 0-2 Lincoln City | Sky Bet League Two |
| 15 | Tue 2 Oct 2018 | 12-2 v MorecambeCheltenham Town 2-2 Morecambe | Sky Bet League Two |
| 16 | Sat 6 Oct 2018 | 10-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 20 Oct 2018 | 11-1 v Forest Green RoversForest Green Rovers 1-1 Cheltenham Town | Sky Bet League Two |
| 18 | Tue 23 Oct 2018 | 10-2 v Oldham AthleticOldham Athletic 2-0 Cheltenham Town | Sky Bet League Two |
| 19 | Sat 27 Oct 2018 | 10-2 v StevenageCheltenham Town 0-2 Stevenage | Sky Bet League Two |
| 20 | Sat 3 Nov 2018 | 12-2 v Mansfield TownCheltenham Town 2-2 Mansfield Town | Sky Bet League Two |
| 21 | Sat 10 Nov 2018 | 10-0 v Ebbsfleet UnitedEbbsfleet United 0-0 Cheltenham Town | Emirates FA Cup First Round |
| 22 | Tue 13 Nov 2018 | 12-0 v Coventry CityCheltenham Town 2-0 Coventry City | Checkatrade Trophy Southern Group E |
| 23 | Sat 17 Nov 2018 | 13-0 v Notts CountyNotts County 0-3 Cheltenham Town | Sky Bet League Two |
| 24 | Tue 20 Nov 2018 | 12-0 v Ebbsfleet UnitedCheltenham Town 2-0 Ebbsfleet United | Emirates FA Cup First Round Replay |
| 25 | Sat 24 Nov 2018 | 1 2-1 v Newport CountyCheltenham Town 2-1 Newport County | Sky Bet League Two |
| 26 | Tue 27 Nov 2018 | 11-4 v BuryBury 4-1 Cheltenham Town | Sky Bet League Two |
| 27 | Sat 1 Dec 2018 | 11-3 v Accrington StanleyAccrington Stanley 3-1 Cheltenham Town | Emirates FA Cup Second Round |
| 28 | Tue 4 Dec 2018 | 11-1 v Newport CountyCheltenham Town 1-1 Newport County | Checkatrade Trophy Second Round |
| 29 | Sat 8 Dec 2018 | 12-1 v Grimsby TownCheltenham Town 2-1 Grimsby Town | Sky Bet League Two |
| 30 | Sat 15 Dec 2018 | 12-2 v Port ValePort Vale 2-2 Cheltenham Town | Sky Bet League Two |
| 31 | Sat 22 Dec 2018 | 10-0 v Swindon TownSwindon Town 0-0 Cheltenham Town | Sky Bet League Two |
| 32 | Wed 26 Dec 2018 | 13-1 v Milton Keynes DonsCheltenham Town 3-1 Milton Keynes Dons | Sky Bet League Two |
| 33 | Sat 29 Dec 2018 | 12-2 v Forest Green RoversCheltenham Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 34 | Tue 1 Jan 2019 | 14-1 v Yeovil TownYeovil Town 1-4 Cheltenham Town | Sky Bet League Two |
| 35 | Sat 5 Jan 2019 | 10-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 36 | Tue 8 Jan 2019 | 11-1 v Oxford UnitedCheltenham Town 1-1 Oxford United | Checkatrade Trophy Second Round |
| 37 | Sat 12 Jan 2019 | 11-3 v Tranmere RoversCheltenham Town 1-3 Tranmere Rovers | Sky Bet League Two |
| 38 | Sat 19 Jan 2019 | 10-2 v Carlisle UnitedCarlisle United 2-0 Cheltenham Town | Sky Bet League Two |
| 39 | Sat 26 Jan 2019 | 13-2 v Macclesfield TownCheltenham Town 3-2 Macclesfield Town | Sky Bet League Two |
| 40 | Tue 5 Feb 2019 | 11-0 v Yeovil TownCheltenham Town 1-0 Yeovil Town | Sky Bet League Two |
| 41 | Sat 9 Feb 2019 | 10-3 v Colchester UnitedColchester United 3-0 Cheltenham Town | Sky Bet League Two |
| 42 | Sat 16 Feb 2019 | 10-1 v Grimsby TownGrimsby Town 1-0 Cheltenham Town | Sky Bet League Two |
| 43 | Tue 19 Feb 2019 | 12-0 v Cambridge UnitedCheltenham Town 2-0 Cambridge United | Sky Bet League Two |
| 44 | Sat 23 Feb 2019 | 11-0 v Port ValeCheltenham Town 1-0 Port Vale | Sky Bet League Two |
| 45 | Sat 2 Mar 2019 | 12-4 v Mansfield TownMansfield Town 4-2 Cheltenham Town | Sky Bet League Two |
| 46 | Tue 5 Mar 2019 | 11-1 v BuryCheltenham Town 1-1 Bury | Sky Bet League Two |
| 47 | Sat 9 Mar 2019 | 14-1 v Notts CountyCheltenham Town 4-1 Notts County | Sky Bet League Two |
| 48 | Fri 15 Mar 2019 | 10-1 v Newport CountyNewport County 1-0 Cheltenham Town | Sky Bet League Two |
| 49 | Sat 23 Mar 2019 | 13-1 v Northampton TownCheltenham Town 3-1 Northampton Town | Sky Bet League Two |
| 50 | Sat 30 Mar 2019 | 13-1 v Crewe AlexandraCrewe Alexandra 1-3 Cheltenham Town | Sky Bet League Two |
| 51 | Sat 6 Apr 2019 | 11-1 v Exeter CityCheltenham Town 1-1 Exeter City | Sky Bet League Two |
| 52 | Sat 13 Apr 2019 | 11-1 v Lincoln CityLincoln City 1-1 Cheltenham Town | Sky Bet League Two |
| 53 | Fri 19 Apr 2019 | 10-0 v Oldham AthleticCheltenham Town 0-0 Oldham Athletic | Sky Bet League Two |
| 54 | Mon 22 Apr 2019 | 10-4 v MorecambeMorecambe 4-0 Cheltenham Town | Sky Bet League Two |
| 55 | Sat 27 Apr 2019 | 13-2 v Swindon TownCheltenham Town 3-2 Swindon Town | Sky Bet League Two |
| 56 | Sat 4 May 2019 | 10-2 v StevenageStevenage 2-0 Cheltenham Town | Sky Bet League Two |
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