| 1 | Tue 12 Nov | 83-3 v WhitehavenWorkington AFC 3-3 Whitehaven | Cumberland Senior Cup Second Round |
| 2 | Sat 16 Nov | 82-2 v FC United of ManchesterFC United of Manchester 2-2 Workington AFC | Northern Premier League - Premier Division |
| 3 | Sat 23 Nov | 83-1 v MickleoverMickleover 1-3 Workington AFC | Northern Premier League - Premier Division |
| 4 | Sat 30 Nov | 80-1 v MacclesfieldWorkington AFC 0-1 Macclesfield | Northern Premier League - Premier Division |
| 5 | Sat 14 Dec | 81-2 v Warrington RylandsWarrington Rylands 2-1 Workington AFC | Northern Premier League - Premier Division |
| 6 | Sat 21 Dec | 81-1 v Lancaster CityLancaster City 1-1 Workington AFC | Northern Premier League - Premier Division |
| 7 | Thu 26 Dec | 82-2 v Morpeth TownWorkington AFC 2-2 Morpeth Town | Northern Premier League - Premier Division |
| 8 | Sat 18 Jan | 84-2 v Matlock TownWorkington AFC 4-2 Matlock Town | Northern Premier League - Premier Division |
| 9 | Tue 21 Jan | 81-3 v Carlisle CityCarlisle City 3-1 Workington AFC | Cumberland Senior Cup Quarter Final |
| 10 | Sat 25 Jan | 8 3-1 v Whitby TownWhitby Town 1-3 Workington AFC | Northern Premier League - Premier Division |
| 11 | Sat 1 Feb | 81-3 v Stockton TownWorkington AFC 1-3 Stockton Town | Northern Premier League - Premier Division |
| 12 | Sat 8 Feb | 80-1 v Ilkeston TownIlkeston Town 1-0 Workington AFC | Northern Premier League - Premier Division |
| 13 | Tue 11 Feb | 142-1 v Bamber BridgeBamber Bridge 1-2 Workington AFC | Northern Premier League - Premier Division |
| 14 | Sat 15 Feb | 101-0 v Hyde UnitedWorkington AFC 1-0 Hyde United | Northern Premier League - Premier Division |
| 15 | Sat 22 Feb | 102-4 v Worksop TownWorksop Town 4-2 Workington AFC | Northern Premier League - Premier Division |
| 16 | Sat 1 Mar | 80-1 v FC United of ManchesterWorkington AFC 0-1 FC United of Manchester | Northern Premier League - Premier Division |
| 17 | Sat 8 Mar | 84-1 v Blyth SpartansWorkington AFC 4-1 Blyth Spartans | Northern Premier League - Premier Division |
| 18 | Sat 15 Mar | 151-1 v Gainsborough TrinityWorkington AFC 1-1 Gainsborough Trinity | Northern Premier League - Premier Division |
| 19 | Sat 22 Mar | 101-2 v Basford UnitedBasford United 2-1 Workington AFC | Northern Premier League - Premier Division |
| 20 | Sat 29 Mar | 163-0 v MickleoverWorkington AFC 3-0 Mickleover | Northern Premier League - Premier Division |
| 21 | Sat 12 Apr | 100-1 v Leek TownLeek Town 1-0 Workington AFC | Northern Premier League - Premier Division |
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