| 1 | Tue 2 Jul | 101-2 v WhitehavenWhitehaven 2-1 Workington AFC | Friendly |
| 2 | Sat 6 Jul | 104-0 v Coppull UnitedCoppull United 0-4 Workington AFC | Friendly |
| 3 | Tue 9 Jul | 172-1 v Carlisle CityWorkington AFC 2-1 Carlisle City | Friendly |
| 4 | Sat 13 Jul | 100-0 v Carlisle UnitedWorkington AFC 0-0 Carlisle United | Friendly |
| 5 | Tue 16 Jul | 161-2 v PenrithPenrith 2-1 Workington AFC | Friendly |
| 6 | Sat 20 Jul | 101-1 v MorecambeWorkington AFC 1-1 Morecambe | Friendly |
| 7 | Tue 30 Jul | 111-0 v Bolton WanderersWorkington AFC 1-0 Bolton Wanderers | Friendly |
| 8 | Sat 3 Aug | 111-3 v ClitheroeClitheroe 3-1 Workington AFC | Friendly |
| 9 | Sat 10 Aug | 110-2 v GuiseleyGuiseley 2-0 Workington AFC | Northern Premier League - Premier Division |
| 10 | Tue 13 Aug | 31-1 v Lancaster CityWorkington AFC 1-1 Lancaster City | Northern Premier League - Premier Division |
| 11 | Sat 17 Aug | 31-1 v Leek TownWorkington AFC 1-1 Leek Town | Northern Premier League - Premier Division |
| 12 | Tue 20 Aug | 112-0 v Prescot CablesPrescot Cables 0-2 Workington AFC | Northern Premier League - Premier Division |
| 13 | Sat 24 Aug | 110-3 v Ashton UnitedAshton United 3-0 Workington AFC | Northern Premier League - Premier Division |
| 14 | Mon 26 Aug | 72-1 v Hebburn TownWorkington AFC 2-1 Hebburn Town | Northern Premier League - Premier Division |
| 15 | Sat 31 Aug | 10 0-1 v Hebburn TownWorkington AFC 0-1 Hebburn Town | Emirates FA Cup First Qualifying Round |
| 16 | Sat 7 Sep | 3 1-1 v Warrington RylandsWorkington AFC 1-1 Warrington Rylands | Northern Premier League - Premier Division |
| 17 | Tue 10 Sep | 10 0-1 v Blyth SpartansBlyth Spartans 1-0 Workington AFC | Northern Premier League - Premier Division |
| 18 | Sat 14 Sep | 151-2 v Matlock TownMatlock Town 2-1 Workington AFC | Northern Premier League - Premier Division |
| 19 | Tue 17 Sep | 141-2 v Bamber BridgeWorkington AFC 1-2 Bamber Bridge | Northern Premier League - Premier Division |
| 20 | Sat 28 Sep | 155-0 v Mirehouse AFCMirehouse AFC 0-5 Workington AFC | Cumberland Senior Cup First Round |
| 21 | Sat 5 Oct | 103-1 v Morpeth TownWorkington AFC 3-1 Morpeth Town | Isuzu FA Trophy Third Qualifying Round |
| 22 | Sat 12 Oct | 82-1 v Ilkeston TownWorkington AFC 2-1 Ilkeston Town | Northern Premier League - Premier Division |
| 23 | Sat 19 Oct | 82-3 v Hyde UnitedHyde United 3-2 Workington AFC | Northern Premier League - Premier Division |
| 24 | Wed 23 Oct | 100-5 v Stockton TownStockton Town 5-0 Workington AFC | Northern Premier League - Premier Division |
| 25 | Sat 26 Oct | 142-3 v Bamber BridgeWorkington AFC 2-3 Bamber Bridge | Isuzu FA Trophy First Round |
| 26 | Sat 2 Nov | 11 2-1 v Worksop TownWorkington AFC 2-1 Worksop Town | Northern Premier League - Premier Division |
| 27 | Tue 12 Nov | 103-3 v WhitehavenWorkington AFC 3-3 Whitehaven | Cumberland Senior Cup Second Round |
| 28 | Sat 16 Nov | 102-2 v FC United of ManchesterFC United of Manchester 2-2 Workington AFC | Northern Premier League - Premier Division |
| 29 | Sat 23 Nov | 103-1 v MickleoverMickleover 1-3 Workington AFC | Northern Premier League - Premier Division |
| 30 | Tue 26 Nov | 102-0 v Basford UnitedWorkington AFC 2-0 Basford United | Northern Premier League - Premier Division |
| 31 | Sat 30 Nov | 110-1 v MacclesfieldWorkington AFC 0-1 Macclesfield | Northern Premier League - Premier Division |
| 32 | Sat 14 Dec | 111-2 v Warrington RylandsWarrington Rylands 2-1 Workington AFC | Northern Premier League - Premier Division |
| 33 | Sat 21 Dec | 151-1 v Lancaster CityLancaster City 1-1 Workington AFC | Northern Premier League - Premier Division |
| 34 | Thu 26 Dec | 102-2 v Morpeth TownWorkington AFC 2-2 Morpeth Town | Northern Premier League - Premier Division |
| 35 | Wed 1 Jan | 8 1-3 v Hebburn TownHebburn Town 3-1 Workington AFC | Northern Premier League - Premier Division |
| 36 | Sat 4 Jan | 80-2 v GuiseleyWorkington AFC 0-2 Guiseley | Northern Premier League - Premier Division |
| 37 | Sat 18 Jan | 104-2 v Matlock TownWorkington AFC 4-2 Matlock Town | Northern Premier League - Premier Division |
| 38 | Tue 21 Jan | 101-3 v Carlisle CityCarlisle City 3-1 Workington AFC | Cumberland Senior Cup Quarter Final |
| 39 | Sat 25 Jan | 103-1 v Whitby TownWhitby Town 1-3 Workington AFC | Northern Premier League - Premier Division |
| 40 | Sat 1 Feb | 101-3 v Stockton TownWorkington AFC 1-3 Stockton Town | Northern Premier League - Premier Division |
| 41 | Sat 8 Feb | 30-1 v Ilkeston TownIlkeston Town 1-0 Workington AFC | Northern Premier League - Premier Division |
| 42 | Tue 11 Feb | 102-1 v Bamber BridgeBamber Bridge 1-2 Workington AFC | Northern Premier League - Premier Division |
| 43 | Sat 15 Feb | 111-0 v Hyde UnitedWorkington AFC 1-0 Hyde United | Northern Premier League - Premier Division |
| 44 | Sat 22 Feb | 112-4 v Worksop TownWorksop Town 4-2 Workington AFC | Northern Premier League - Premier Division |
| 45 | Sat 1 Mar | 100-1 v FC United of ManchesterWorkington AFC 0-1 FC United of Manchester | Northern Premier League - Premier Division |
| 46 | Sat 8 Mar | 104-1 v Blyth SpartansWorkington AFC 4-1 Blyth Spartans | Northern Premier League - Premier Division |
| 47 | Sat 22 Mar | 15 1-2 v Basford UnitedBasford United 2-1 Workington AFC | Northern Premier League - Premier Division |
| 48 | Sat 29 Mar | 173-0 v MickleoverWorkington AFC 3-0 Mickleover | Northern Premier League - Premier Division |
| 49 | Sat 5 Apr | 142-3 v MacclesfieldMacclesfield 3-2 Workington AFC | Northern Premier League - Premier Division |
| 50 | Sat 19 Apr | 10 2-0 v Prescot CablesWorkington AFC 2-0 Prescot Cables | Northern Premier League - Premier Division |
| 51 | Mon 21 Apr | 100-1 v Morpeth TownMorpeth Town 1-0 Workington AFC | Northern Premier League - Premier Division |
| 52 | Sat 26 Apr | 145-1 v Ashton UnitedWorkington AFC 5-1 Ashton United | Northern Premier League - Premier Division |
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