| 1 | Sat 17 Nov 2018 | 41-4 v Grantham TownWorkington 1-4 Grantham Town |
| 2 | Sat 1 Dec 2018 | 24-2 v Hednesford TownWorkington 4-2 Hednesford Town |
| 3 | Sat 8 Dec 2018 | 5 1-2 v Matlock TownMatlock Town 2-1 Workington |
| 4 | Wed 26 Dec 2018 | 32-0 v Lancaster CityLancaster City 0-2 Workington |
| 5 | Tue 1 Jan 2019 | 51-2 v Stalybridge CelticWorkington 1-2 Stalybridge Celtic |
| 6 | Sat 5 Jan 2019 | 21-1 v Stafford RangersStafford Rangers 1-1 Workington |
| 7 | Sat 12 Jan 2019 | 31-4 v Gainsborough TrinityGainsborough Trinity 4-1 Workington |
| 8 | Sat 19 Jan 2019 | 52-1 v Bamber BridgeWorkington 2-1 Bamber Bridge |
| 9 | Sat 2 Feb 2019 | 52-0 v Grantham TownGrantham Town 0-2 Workington |
| 10 | Sat 16 Feb 2019 | 50-3 v Basford UnitedWorkington 0-3 Basford United |
| 11 | Tue 26 Feb 2019 | 50-2 v Warrington TownWorkington 0-2 Warrington Town |
| 12 | Sat 2 Mar 2019 | 51-2 v Hyde UnitedWorkington 1-2 Hyde United |
| 13 | Tue 5 Mar 2019 | 50-2 v Farsley CelticFarsley Celtic 2-0 Workington |
| 14 | Sat 23 Mar 2019 | 5 1-0 v Whitby TownWhitby Town 0-1 Workington |
| 15 | Sat 30 Mar 2019 | 52-4 v Nantwich TownWorkington 2-4 Nantwich Town |
| 16 | Tue 2 Apr 2019 | 50-1 v Mickleover SportsWorkington 0-1 Mickleover Sports |
| 17 | Sat 6 Apr 2019 | 3 0-2 v Witton AlbionWitton Albion 2-0 Workington |
| 18 | Tue 9 Apr 2019 | 30-2 v South ShieldsWorkington 0-2 South Shields |
| 19 | Mon 22 Apr 2019 | 50-2 v Lancaster CityWorkington 0-2 Lancaster City |
| 20 | Sat 27 Apr 2019 | 51-5 v Scarborough AthleticScarborough Athletic 5-1 Workington |
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