| 1 | Sat 15 Jul | 50-3 v Carlisle UnitedWorkington AFC 0-3 Carlisle United | Friendly |
| 2 | Sat 22 Jul | 56-1 v Whitley BayWhitley Bay 1-6 Workington AFC | Friendly |
| 3 | Tue 25 Jul | 143-1 v PenrithWorkington AFC 3-1 Penrith | Friendly |
| 4 | Sat 29 Jul | 53-0 v Ashington AFCAshington AFC 0-3 Workington AFC | Friendly |
| 5 | Sat 5 Aug | 55-0 v DunstonDunston 0-5 Workington AFC | Friendly |
| 6 | Sat 12 Aug | 55-0 v Ashton UnitedWorkington AFC 5-0 Ashton United | Northern Premier League - Premier Division |
| 7 | Tue 22 Aug | 51-4 v RadcliffeWorkington AFC 1-4 Radcliffe | Northern Premier League - Premier Division |
| 8 | Sat 26 Aug | 52-1 v Stafford RangersWorkington AFC 2-1 Stafford Rangers | Northern Premier League - Premier Division |
| 9 | Mon 28 Aug | 5 0-3 v Bamber BridgeBamber Bridge 3-0 Workington AFC | Northern Premier League - Premier Division |
| 10 | Sat 2 Sep | 56-0 v Prestwich HeysWorkington AFC 6-0 Prestwich Heys | Emirates FA Cup First Qualifying Round |
| 11 | Sat 9 Sep | 55-3 v Basford UnitedWorkington AFC 5-3 Basford United | Northern Premier League - Premier Division |
| 12 | Fri 15 Sep | 51-3 v DarlingtonDarlington 3-1 Workington AFC | Emirates FA Cup Second Qualifying Round |
| 13 | Tue 26 Sep | 52-1 v Lancaster CityWorkington AFC 2-1 Lancaster City | Northern Premier League - Premier Division |
| 14 | Sat 30 Sep | 52-1 v FC United of ManchesterWorkington AFC 2-1 FC United of Manchester | Northern Premier League - Premier Division |
| 15 | Sat 7 Oct | 51-3 v Hyde UnitedWorkington AFC 1-3 Hyde United | Isuzu FA Trophy Third Qualifying Round |
| 16 | Sat 21 Oct | 100-4 v Charlton AthleticCharlton Athletic 4-0 Reading | Sky Bet League One |
| 17 | Tue 24 Oct | 101-2 v Fleetwood TownReading 1-2 Fleetwood Town | Sky Bet League One |
| 18 | Sat 28 Oct | 102-3 v PortsmouthReading 2-3 Portsmouth | Sky Bet League One |
| 19 | Tue 7 Nov | 101-1 v Bristol RoversReading 1-1 Bristol Rovers | Sky Bet League One |
| 20 | Sat 11 Nov | 102-3 v Shrewsbury TownShrewsbury Town 3-2 Reading | Sky Bet League One |
| 21 | Sat 25 Nov | 102-1 v Wycombe WanderersWycombe Wanderers 1-2 Reading | Sky Bet League One |
| 22 | Tue 28 Nov | 105-1 v Carlisle UnitedReading 5-1 Carlisle United | Sky Bet League One |
| 23 | Wed 6 Dec | 101-1 v Charlton AthleticReading 1-1 Charlton Athletic | EFL Trophy Second Round |
| 24 | Sat 9 Dec | 10 1-3 v BarnsleyReading 1-3 Barnsley | Sky Bet League One |
| 25 | Tue 12 Dec | 53-3 v Worksop TownWorkington AFC 3-3 Worksop Town | Northern Premier League - Premier Division |
| 26 | Tue 12 Dec | 101-1 v Oxford UnitedReading 1-1 Oxford United | Sky Bet League One |
| 27 | Sat 16 Dec | 101-1 v Lincoln CityLincoln City 1-1 Reading | Sky Bet League One |
| 28 | Sat 23 Dec | 102-0 v Wigan AthleticReading 2-0 Wigan Athletic | Sky Bet League One |
| 29 | Fri 29 Dec | 10 2-2 v Cheltenham TownCheltenham Town 2-2 Reading | Sky Bet League One |
| 30 | Mon 1 Jan | 103-2 v Exeter CityReading 3-2 Exeter City | Sky Bet League One |
| 31 | Sat 20 Jan | 100-1 v Wigan AthleticWigan Athletic 1-0 Reading | Sky Bet League One |
| 32 | Sat 20 Jan | 3 2-2 v Warrington RylandsWorkington AFC 2-2 Warrington Rylands | Northern Premier League - Premier Division |
| 33 | Tue 23 Jan | 101-0 v Derby CountyReading 1-0 Derby County | Sky Bet League One |
| 34 | Sat 27 Jan | 10 1-1 v Leyton OrientReading 1-1 Leyton Orient | Sky Bet League One |
| 35 | Sat 27 Jan | 3 0-0 v Whitby TownWorkington AFC 0-0 Whitby Town | Northern Premier League - Premier Division |
| 36 | Tue 30 Jan | 123-0 v Unisun AthleticWorkington AFC 3-0 Unisun Athletic | Cumberland Senior Cup Quarter Final |
| 37 | Sat 3 Feb | 101-1 v Oxford UnitedOxford United 1-1 Reading | Sky Bet League One |
| 38 | Tue 6 Feb | 101-0 v StevenageStevenage 0-1 Reading | Sky Bet League One |
| 39 | Sat 10 Feb | 102-0 v Charlton AthleticReading 2-0 Charlton Athletic | Sky Bet League One |
| 40 | Sat 10 Feb | 50-2 v Bradford (Park Avenue)Workington AFC 0-2 Bradford (Park Avenue) | Northern Premier League - Premier Division |
| 41 | Sat 17 Feb | 101-4 v PortsmouthPortsmouth 4-1 Reading | Sky Bet League One |
| 42 | Sat 17 Feb | 51-1 v Lancaster CityLancaster City 1-1 Workington AFC | Northern Premier League - Premier Division |
| 43 | Tue 20 Feb | 102-0 v Port ValeReading 2-0 Port Vale | Sky Bet League One |
| 44 | Sat 24 Feb | 10 2-3 v Shrewsbury TownReading 2-3 Shrewsbury Town | Sky Bet League One |
| 45 | Sat 24 Feb | 52-1 v Matlock TownWorkington AFC 2-1 Matlock Town | Northern Premier League - Premier Division |
| 46 | Sat 2 Mar | 103-1 v Carlisle UnitedCarlisle United 1-3 Reading | Sky Bet League One |
| 47 | Sat 2 Mar | 53-1 v FC United of ManchesterFC United of Manchester 1-3 Workington AFC | Northern Premier League - Premier Division |
| 48 | Sat 9 Mar | 101-2 v Wycombe WanderersReading 1-2 Wycombe Wanderers | Sky Bet League One |
| 49 | Sat 9 Mar | 5 0-1 v Hyde UnitedWorkington AFC 0-1 Hyde United | Northern Premier League - Premier Division |
| 50 | Tue 12 Mar | 101-2 v Derby CountyDerby County 2-1 Reading | Sky Bet League One |
| 51 | Sat 16 Mar | 104-0 v Cambridge UnitedReading 4-0 Cambridge United | Sky Bet League One |
| 52 | Sat 23 Mar | 52-4 v Gainsborough TrinityGainsborough Trinity 4-2 Workington AFC | Northern Premier League - Premier Division |
| 53 | Fri 29 Mar | 101-0 v Northampton TownReading 1-0 Northampton Town | Sky Bet League One |
| 54 | Sat 30 Mar | 50-1 v Stafford RangersStafford Rangers 1-0 Workington AFC | Northern Premier League - Premier Division |
| 55 | Mon 1 Apr | 102-5 v Bolton WanderersBolton Wanderers 5-2 Reading | Sky Bet League One |
| 56 | Sat 6 Apr | 101-1 v Lincoln CityReading 1-1 Lincoln City | Sky Bet League One |
| 57 | Sat 6 Apr | 51-2 v Worksop TownWorksop Town 2-1 Workington AFC | Northern Premier League - Premier Division |
| 58 | Tue 9 Apr | 102-0 v Bristol RoversBristol Rovers 0-2 Reading | Sky Bet League One |
| 59 | Sat 13 Apr | 102-2 v BarnsleyBarnsley 2-2 Reading | Sky Bet League One |
| 60 | Sat 13 Apr | 50-3 v MarineWorkington AFC 0-3 Marine | Northern Premier League - Premier Division |
| 61 | Sat 20 Apr | 102-3 v Burton AlbionBurton Albion 3-2 Reading | Sky Bet League One |
| 62 | Sat 20 Apr | 50-2 v MacclesfieldMacclesfield 2-0 Workington AFC | Northern Premier League - Premier Division |
| 63 | Tue 23 Apr | 51-0 v Carlisle UnitedWorkington AFC 1-0 Carlisle United | Cumberland Senior Cup Final |
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