| 1 | Sat 5 Sep 2020 | 54-3 v Lancaster CityWorkington AFC 4-3 Lancaster City | Friendly |
| 2 | Sat 12 Sep 2020 | 53-1 v Knaresborough TownKnaresborough Town 1-3 Workington AFC | Emirates FA Cup Preliminary Round |
| 3 | Sat 19 Sep 2020 | 52-2 v Pickering TownPickering Town 2-2 Workington AFC | Northern Premier League - North West Division |
| 4 | Tue 22 Sep 2020 | 5 3-5 v RadcliffeRadcliffe 5-3 Workington AFC | Emirates FA Cup First Qualifying Round |
| 5 | Sat 26 Sep 2020 | 50-0 v Kendal TownKendal Town 0-0 Workington AFC | Northern Premier League - North West Division |
| 6 | Sat 3 Oct 2020 | 55-2 v City of LiverpoolWorkington AFC 5-2 City of Liverpool | Northern Premier League - North West Division |
| 7 | Tue 6 Oct 2020 | 5 1-0 v ColneColne 0-1 Workington AFC | Northern Premier League - North West Division |
| 8 | Sat 10 Oct 2020 | 52-0 v MossleyWorkington AFC 2-0 Mossley | Northern Premier League - North West Division |
| 9 | Sat 17 Oct 2020 | 54-1 v Pontefract CollieriesPontefract Collieries 1-4 Workington AFC | Buildbase FA Trophy Second Qualifying Round |
| 10 | Tue 20 Oct 2020 | 290-1 v Leyton OrientTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 11 | Tue 20 Oct 2020 | 52-1 v ClitheroeWorkington AFC 2-1 Clitheroe | Northern Premier League - North West Division |
| 12 | Sat 24 Oct 2020 | 292-0 v Southend UnitedTranmere Rovers 2-0 Southend United | Sky Bet League Two |
| 13 | Sat 24 Oct 2020 | 53-0 v Ossett UnitedOssett United 0-3 Workington AFC | Northern Premier League - North West Division |
| 14 | Tue 27 Oct 2020 | 29 0-4 v Crawley TownCrawley Town 4-0 Tranmere Rovers | Sky Bet League Two |
| 15 | Sat 31 Oct 2020 | 290-1 v MorecambeTranmere Rovers 0-1 Morecambe | Sky Bet League Two |
| 16 | Wed 11 Nov 2020 | 292-2 v Wigan AthleticTranmere Rovers 2-2 Wigan Athletic | Papa John’s Trophy Northern Group D |
| 17 | Sat 14 Nov 2020 | 294-3 v Port ValePort Vale 3-4 Tranmere Rovers | Sky Bet League Two |
| 18 | Tue 8 Dec 2020 | 51-3 v Nantwich TownNantwich Town 3-1 Workington AFC | Buildbase FA Trophy First Round |
| 19 | Sat 19 Dec 2020 | 52-2 v Brighouse TownBrighouse Town 2-2 Workington AFC | Northern Premier League - North West Division |
| 20 | Sat 30 Jan 2021 | 90-0 v Forest Green RoversForest Green Rovers 0-0 Cheltenham Town | Sky Bet League Two |
| 21 | Tue 16 Feb 2021 | 92-1 v WalsallWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 20 Feb 2021 | 90-2 v Bradford CityCheltenham Town 0-2 Bradford City | Sky Bet League Two |
| 23 | Tue 23 Feb 2021 | 91-0 v Cambridge UnitedCambridge United 0-1 Cheltenham Town | Sky Bet League Two |
| 24 | Sat 27 Feb 2021 | 92-0 v Scunthorpe UnitedScunthorpe United 0-2 Cheltenham Town | Sky Bet League Two |
| 25 | Tue 2 Mar 2021 | 91-0 v Southend UnitedCheltenham Town 1-0 Southend United | Sky Bet League Two |
| 26 | Sat 6 Mar 2021 | 93-2 v Port ValeCheltenham Town 3-2 Port Vale | Sky Bet League Two |
| 27 | Tue 9 Mar 2021 | 91-3 v Mansfield TownMansfield Town 3-1 Cheltenham Town | Sky Bet League Two |
| 28 | Sat 13 Mar 2021 | 91-0 v Exeter CityExeter City 0-1 Cheltenham Town | Sky Bet League Two |
| 29 | Tue 16 Mar 2021 | 90-2 v BarrowCheltenham Town 0-2 Barrow | Sky Bet League Two |
| 30 | Sat 20 Mar 2021 | 92-0 v Salford CityCheltenham Town 2-0 Salford City | Sky Bet League Two |
| 31 | Sat 27 Mar 2021 | 90-1 v MorecambeMorecambe 1-0 Cheltenham Town | Sky Bet League Two |
| 32 | Fri 2 Apr 2021 | 9 4-0 v Tranmere RoversCheltenham Town 4-0 Tranmere Rovers | Sky Bet League Two |
| 33 | Mon 5 Apr 2021 | 91-1 v Grimsby TownGrimsby Town 1-1 Cheltenham Town | Sky Bet League Two |
| 34 | Sat 10 Apr 2021 | 91-0 v Leyton OrientCheltenham Town 1-0 Leyton Orient | Sky Bet League Two |
| 35 | Fri 16 Apr 2021 | 90-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
| 36 | Tue 20 Apr 2021 | 91-0 v StevenageStevenage 0-1 Cheltenham Town | Sky Bet League Two |
| 37 | Sat 24 Apr 2021 | 91-0 v Colchester UnitedCheltenham Town 1-0 Colchester United | Sky Bet League Two |
| 38 | Tue 27 Apr 2021 | 91-1 v Carlisle UnitedCheltenham Town 1-1 Carlisle United | Sky Bet League Two |
| 39 | Sat 1 May 2021 | 90-1 v Newport CountyNewport County 1-0 Cheltenham Town | Sky Bet League Two |
| 40 | Sat 8 May 2021 | 94-1 v Harrogate TownCheltenham Town 4-1 Harrogate Town | Sky Bet League Two |
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