| 1 | Sat 5 Sep 2020 | 41-0 v Peterborough UnitedPeterborough United 0-1 Cheltenham Town | Carabao Cup First Round South |
| 2 | Tue 15 Sep 2020 | 41-3 v MillwallMillwall 3-1 Cheltenham Town | Carabao Cup Second Round |
| 3 | Sat 19 Sep 2020 | 43-0 v Tranmere RoversTranmere Rovers 0-3 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 42-0 v Leyton OrientLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 6 Oct 2020 | 42-0 v Plymouth ArgyleCheltenham Town 2-0 Plymouth Argyle | Papa John’s Trophy Group 9 |
| 6 | Sat 10 Oct 2020 | 42-0 v Crawley TownCheltenham Town 2-0 Crawley Town | Sky Bet League Two |
| 7 | Tue 13 Oct 2020 | 41-3 v Grimsby TownCheltenham Town 1-3 Grimsby Town | Sky Bet League Two |
| 8 | Sat 17 Oct 2020 | 42-0 v Southend UnitedSouthend United 0-2 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 20 Oct 2020 | 41-0 v Scunthorpe UnitedCheltenham Town 1-0 Scunthorpe United | Sky Bet League Two |
| 10 | Sat 24 Oct 2020 | 40-0 v Mansfield TownCheltenham Town 0-0 Mansfield Town | Sky Bet League Two |
| 11 | Tue 27 Oct 2020 | 41-2 v Port ValePort Vale 2-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 31 Oct 2020 | 42-1 v Forest Green RoversCheltenham Town 2-1 Forest Green Rovers | Sky Bet League Two |
| 13 | Tue 3 Nov 2020 | 41-2 v Oldham AthleticOldham Athletic 2-1 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 14 Nov 2020 | 42-1 v Carlisle UnitedCarlisle United 1-2 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 21 Nov 2020 | 43-0 v WalsallCheltenham Town 3-0 Walsall | Sky Bet League Two |
| 16 | Tue 24 Nov 2020 | 41-1 v Cambridge UnitedCheltenham Town 1-1 Cambridge United | Sky Bet League Two |
| 17 | Tue 1 Dec 2020 | 42-1 v Bradford CityBradford City 1-2 Cheltenham Town | Sky Bet League Two |
| 18 | Sat 5 Dec 2020 | 45-3 v Exeter CityCheltenham Town 5-3 Exeter City | Sky Bet League Two |
| 19 | Tue 8 Dec 2020 | 4 0-3 v PortsmouthCheltenham Town 0-3 Portsmouth | Papa John’s Trophy Second Round |
| 20 | Sat 12 Dec 2020 | 40-0 v Salford CitySalford City 0-0 Cheltenham Town | Sky Bet League Two |
| 21 | Tue 15 Dec 2020 | 40-1 v Bolton WanderersCheltenham Town 0-1 Bolton Wanderers | Sky Bet League Two |
| 22 | Sat 19 Dec 2020 | 40-3 v BarrowBarrow 3-0 Cheltenham Town | Sky Bet League Two |
| 23 | Sat 26 Dec 2020 | 41-1 v StevenageCheltenham Town 1-1 Stevenage | Sky Bet League Two |
| 24 | Tue 29 Dec 2020 | 40-0 v Colchester UnitedColchester United 0-0 Cheltenham Town | Sky Bet League Two |
| 25 | Sun 10 Jan 2021 | 42-1 v Mansfield TownCheltenham Town 2-1 Mansfield Town | Emirates FA Cup Third Round |
| 26 | Sat 16 Jan 2021 | 41-1 v Bolton WanderersBolton Wanderers 1-1 Cheltenham Town | Sky Bet League Two |
| 27 | Tue 19 Jan 2021 | 4 1-1 v Newport CountyCheltenham Town 1-1 Newport County | Sky Bet League Two |
| 28 | Sat 23 Jan 2021 | 4 1-3 v Manchester CityCheltenham Town 1-3 Manchester City | Emirates FA Cup Fourth Round |
| 29 | Tue 26 Jan 2021 | 42-0 v Oldham AthleticCheltenham Town 2-0 Oldham Athletic | Sky Bet League Two |
| 30 | Sat 30 Jan 2021 | 40-0 v Forest Green RoversForest Green Rovers 0-0 Cheltenham Town | Sky Bet League Two |
| 31 | Tue 9 Feb 2021 | 41-0 v Harrogate TownHarrogate Town 0-1 Cheltenham Town | Sky Bet League Two |
| 32 | Tue 16 Feb 2021 | 42-1 v WalsallWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 33 | Sat 20 Feb 2021 | 40-2 v Bradford CityCheltenham Town 0-2 Bradford City | Sky Bet League Two |
| 34 | Tue 23 Feb 2021 | 41-0 v Cambridge UnitedCambridge United 0-1 Cheltenham Town | Sky Bet League Two |
| 35 | Sat 27 Feb 2021 | 42-0 v Scunthorpe UnitedScunthorpe United 0-2 Cheltenham Town | Sky Bet League Two |
| 36 | Tue 2 Mar 2021 | 41-0 v Southend UnitedCheltenham Town 1-0 Southend United | Sky Bet League Two |
| 37 | Sat 6 Mar 2021 | 43-2 v Port ValeCheltenham Town 3-2 Port Vale | Sky Bet League Two |
| 38 | Tue 9 Mar 2021 | 41-3 v Mansfield TownMansfield Town 3-1 Cheltenham Town | Sky Bet League Two |
| 39 | Sat 13 Mar 2021 | 41-0 v Exeter CityExeter City 0-1 Cheltenham Town | Sky Bet League Two |
| 40 | Tue 16 Mar 2021 | 40-2 v BarrowCheltenham Town 0-2 Barrow | Sky Bet League Two |
| 41 | Sat 20 Mar 2021 | 42-0 v Salford CityCheltenham Town 2-0 Salford City | Sky Bet League Two |
| 42 | Sat 27 Mar 2021 | 40-1 v MorecambeMorecambe 1-0 Cheltenham Town | Sky Bet League Two |
| 43 | Fri 2 Apr 2021 | 44-0 v Tranmere RoversCheltenham Town 4-0 Tranmere Rovers | Sky Bet League Two |
| 44 | Mon 5 Apr 2021 | 41-1 v Grimsby TownGrimsby Town 1-1 Cheltenham Town | Sky Bet League Two |
| 45 | Sat 10 Apr 2021 | 41-0 v Leyton OrientCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 46 | Fri 16 Apr 2021 | 40-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 47 | Tue 20 Apr 2021 | 41-0 v StevenageStevenage 0-1 Cheltenham Town | Sky Bet League Two |
| 48 | Sat 24 Apr 2021 | 41-0 v Colchester UnitedCheltenham Town 1-0 Colchester United | Sky Bet League Two |
| 49 | Tue 27 Apr 2021 | 41-1 v Carlisle UnitedCheltenham Town 1-1 Carlisle United | Sky Bet League Two |
| 50 | Sat 1 May 2021 | 4 0-1 v Newport CountyNewport County 1-0 Cheltenham Town | Sky Bet League Two |
| 51 | Sat 8 May 2021 | 44-1 v Harrogate TownCheltenham Town 4-1 Harrogate Town | Sky Bet League Two |
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