| 1 | Sat 21 Jul 2018 | 50-3 v Birmingham CityCheltenham Town 0-3 Birmingham City | Friendly |
| 2 | Sat 4 Aug 2018 | 50-1 v Crawley TownCheltenham Town 0-1 Crawley Town | Sky Bet League Two |
| 3 | Sat 11 Aug 2018 | 50-1 v Tranmere RoversTranmere Rovers 1-0 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 14 Aug 2018 | 52-2 v Colchester UnitedCheltenham Town 2-2 Colchester United | Carabao Cup First Round |
| 5 | Sat 18 Aug 2018 | 50-1 v Carlisle UnitedCheltenham Town 0-1 Carlisle United | Sky Bet League Two |
| 6 | Tue 21 Aug 2018 | 51-1 v Macclesfield TownMacclesfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 7 | Sat 25 Aug 2018 | 51-0 v Cambridge UnitedCambridge United 0-1 Cheltenham Town | Sky Bet League Two |
| 8 | Tue 28 Aug 2018 | 5 0-1 v BrentfordBrentford 1-0 Cheltenham Town | Carabao Cup Second Round |
| 9 | Sat 1 Sep 2018 | 51-3 v Colchester UnitedCheltenham Town 1-3 Colchester United | Sky Bet League Two |
| 10 | Tue 4 Sep 2018 | 50-4 v Forest Green RoversForest Green Rovers 4-0 Cheltenham Town | Checkatrade Trophy Southern Group E |
| 11 | Sat 8 Sep 2018 | 53-1 v Northampton TownNorthampton Town 1-3 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 15 Sep 2018 | 50-0 v Crewe AlexandraCheltenham Town 0-0 Crewe Alexandra | Sky Bet League Two |
| 13 | Sat 22 Sep 2018 | 51-3 v Exeter CityExeter City 3-1 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 29 Sep 2018 | 50-2 v Lincoln CityCheltenham Town 0-2 Lincoln City | Sky Bet League Two |
| 15 | Tue 2 Oct 2018 | 52-2 v MorecambeCheltenham Town 2-2 Morecambe | Sky Bet League Two |
| 16 | Sat 6 Oct 2018 | 50-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 20 Oct 2018 | 51-1 v Forest Green RoversForest Green Rovers 1-1 Cheltenham Town | Sky Bet League Two |
| 18 | Tue 23 Oct 2018 | 50-2 v Oldham AthleticOldham Athletic 2-0 Cheltenham Town | Sky Bet League Two |
| 19 | Sat 27 Oct 2018 | 50-2 v StevenageCheltenham Town 0-2 Stevenage | Sky Bet League Two |
| 20 | Sat 10 Nov 2018 | 50-0 v Ebbsfleet UnitedEbbsfleet United 0-0 Cheltenham Town | Emirates FA Cup First Round |
| 21 | Tue 4 Dec 2018 | 51-1 v Newport CountyCheltenham Town 1-1 Newport County | Checkatrade Trophy Second Round |
| 22 | Sat 8 Dec 2018 | 5 2-1 v Grimsby TownCheltenham Town 2-1 Grimsby Town | Sky Bet League Two |
| 23 | Sat 15 Dec 2018 | 52-2 v Port ValePort Vale 2-2 Cheltenham Town | Sky Bet League Two |
| 24 | Sat 29 Dec 2018 | 52-2 v Forest Green RoversCheltenham Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 25 | Tue 1 Jan 2019 | 5 4-1 v Yeovil TownYeovil Town 1-4 Cheltenham Town | Sky Bet League Two |
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