| 1 | Sat 8 Dec 2018 | 21-2 v Matlock TownMatlock Town 2-1 Workington |
| 2 | Sat 22 Dec 2018 | 5 2-3 v Scarborough AthleticWorkington 2-3 Scarborough Athletic |
| 3 | Wed 26 Dec 2018 | 52-0 v Lancaster CityLancaster City 0-2 Workington |
| 4 | Sat 12 Jan 2019 | 21-4 v Gainsborough TrinityGainsborough Trinity 4-1 Workington |
| 5 | Sat 19 Jan 2019 | 22-1 v Bamber BridgeWorkington 2-1 Bamber Bridge |
| 6 | Sat 2 Feb 2019 | 22-0 v Grantham TownGrantham Town 0-2 Workington |
| 7 | Sat 16 Feb 2019 | 20-3 v Basford UnitedWorkington 0-3 Basford United |
| 8 | Tue 19 Feb 2019 | 20-2 v Witton AlbionWorkington 0-2 Witton Albion |
| 9 | Sat 23 Feb 2019 | 22-0 v MarineMarine 0-2 Workington |
| 10 | Tue 26 Feb 2019 | 20-2 v Warrington TownWorkington 0-2 Warrington Town |
| 11 | Sat 2 Mar 2019 | 21-2 v Hyde UnitedWorkington 1-2 Hyde United |
| 12 | Tue 5 Mar 2019 | 20-2 v Farsley CelticFarsley Celtic 2-0 Workington |
| 13 | Sat 23 Mar 2019 | 21-0 v Whitby TownWhitby Town 0-1 Workington |
| 14 | Sat 30 Mar 2019 | 22-4 v Nantwich TownWorkington 2-4 Nantwich Town |
| 15 | Tue 2 Apr 2019 | 20-1 v Mickleover SportsWorkington 0-1 Mickleover Sports |
| 16 | Sat 6 Apr 2019 | 20-2 v Witton AlbionWitton Albion 2-0 Workington |
| 17 | Tue 9 Apr 2019 | 50-2 v South ShieldsWorkington 0-2 South Shields |
| 18 | Sat 13 Apr 2019 | 50-2 v Gainsborough TrinityWorkington 0-2 Gainsborough Trinity |
| 19 | Sat 20 Apr 2019 | 5 2-3 v BuxtonBuxton 3-2 Workington |
| 20 | Mon 22 Apr 2019 | 40-2 v Lancaster CityWorkington 0-2 Lancaster City |
| 21 | Sat 27 Apr 2019 | 41-5 v Scarborough AthleticScarborough Athletic 5-1 Workington |
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