| 1 | Tue 12 Nov | 73-3 v WhitehavenWorkington AFC 3-3 Whitehaven | Cumberland Senior Cup Second Round |
| 2 | Sat 23 Nov | 153-1 v MickleoverMickleover 1-3 Workington AFC | Northern Premier League - Premier Division |
| 3 | Tue 26 Nov | 142-0 v Basford UnitedWorkington AFC 2-0 Basford United | Northern Premier League - Premier Division |
| 4 | Sat 30 Nov | 150-1 v MacclesfieldWorkington AFC 0-1 Macclesfield | Northern Premier League - Premier Division |
| 5 | Sat 14 Dec | 171-2 v Warrington RylandsWarrington Rylands 2-1 Workington AFC | Northern Premier League - Premier Division |
| 6 | Sat 21 Dec | 161-1 v Lancaster CityLancaster City 1-1 Workington AFC | Northern Premier League - Premier Division |
| 7 | Thu 26 Dec | 162-2 v Morpeth TownWorkington AFC 2-2 Morpeth Town | Northern Premier League - Premier Division |
| 8 | Wed 1 Jan | 141-3 v Hebburn TownHebburn Town 3-1 Workington AFC | Northern Premier League - Premier Division |
| 9 | Sat 4 Jan | 140-2 v GuiseleyWorkington AFC 0-2 Guiseley | Northern Premier League - Premier Division |
| 10 | Sat 18 Jan | 174-2 v Matlock TownWorkington AFC 4-2 Matlock Town | Northern Premier League - Premier Division |
| 11 | Tue 21 Jan | 111-3 v Carlisle CityCarlisle City 3-1 Workington AFC | Cumberland Senior Cup Quarter Final |
| 12 | Sat 25 Jan | 143-1 v Whitby TownWhitby Town 1-3 Workington AFC | Northern Premier League - Premier Division |
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