| 1 | 5/9/2020 | 74-3 v Lancaster CityWorkington AFC 4-3 Lancaster City | Friendly |
| 2 | 12/9/2020 | 73-1 v Knaresborough TownKnaresborough Town 1-3 Workington AFC | Emirates FA Cup Preliminary Round |
| 3 | 19/9/2020 | 72-2 v Pickering TownPickering Town 2-2 Workington AFC | Northern Premier League - North West Division |
| 4 | 22/9/2020 | 173-5 v RadcliffeRadcliffe 5-3 Workington AFC | Emirates FA Cup First Qualifying Round |
| 5 | 26/9/2020 | 70-0 v Kendal TownKendal Town 0-0 Workington AFC | Northern Premier League - North West Division |
| 6 | 29/9/2020 | 142-2 v TraffordWorkington AFC 2-2 Trafford | Northern Premier League - North West Division |
| 7 | 3/10/2020 | 14 5-2 v City of LiverpoolWorkington AFC 5-2 City of Liverpool | Northern Premier League - North West Division |
| 8 | 6/10/2020 | 141-0 v ColneColne 0-1 Workington AFC | Northern Premier League - North West Division |
| 9 | 10/10/2020 | 112-0 v MossleyWorkington AFC 2-0 Mossley | Northern Premier League - North West Division |
| 10 | 17/10/2020 | 174-1 v Pontefract CollieriesPontefract Collieries 1-4 Workington AFC | Buildbase FA Trophy Second Qualifying Round |
| 11 | 20/10/2020 | 162-1 v ClitheroeWorkington AFC 2-1 Clitheroe | Northern Premier League - North West Division |
| 12 | 24/10/2020 | 173-0 v Ossett UnitedOssett United 0-3 Workington AFC | Northern Premier League - North West Division |
| 13 | 31/10/2020 | 161-0 v Glossop North EndGlossop North End 0-1 Workington AFC | Buildbase FA Trophy Third Qualifying Round |
| 14 | 8/12/2020 | 91-3 v Nantwich TownNantwich Town 3-1 Workington AFC | Buildbase FA Trophy First Round |
| 15 | 19/12/2020 | 152-2 v Brighouse TownBrighouse Town 2-2 Workington AFC | Northern Premier League - North West Division |
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