Results
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| Competition | Round | Date | Home | | Away | | Venue | Crowd | |
|---|
| Challenge Cup 1956/57 | Round 1 | Feb 9 | Workington | 5 | Oldham | 14 | Derwent Park | | > |
| Challenge Cup 1957/58 | Round 1 | Feb 8 | Workington | 3 | Leigh | 0 | Derwent Park | | > |
| Challenge Cup 1957/58 | Round 3 | Mar 8 | Workington | 11 | Warrington | 0 | Derwent Park | | > |
| Challenge Cup 1958/59 | Round 1 | Feb 21 | Workington | 5 | Featherstone | 8 | Derwent Park | | > |
| Challenge Cup 1959/60 | Round 1 | Feb 13 | Workington | 0 | Featherstone | 15 | Derwent Park | | > |
| Challenge Cup 1960/61 | Round 1 | Feb 11 | Workington | 9 | Barrow | 5 | Derwent Park | | > |
| Challenge Cup 1960/61 | Round 2 | 25 | Workington | 0 | Halifax | 4 | Derwent Park | | > |
| Challenge Cup 1961/62 | Round 1 | Feb 10 | Workington | 14 | Rochdale | 2 | Derwent Park | | > |
| Challenge Cup 1961/62 | Round 3 | Mar 24 | Workington | 3 | Hull KR | 15 | Derwent Park | | > |
| Challenge Cup 1962/63 | Round 2 | Mar 16 | Workington | 0 | Oldham | 13 | Derwent Park | | > |
| Challenge Cup 1963/64 | Round 1 | Feb 8 | Workington | 21 | Warrington | 3 | Derwent Park | | > |
| Challenge Cup 1963/64 | Round 2 | 29 | Workington | 3 | Swinton | 11 | Derwent Park | | > |
| Challenge Cup 1964/65 | Round 1 | Feb 10 | Workington | 2 | Widnes | 0 | Derwent Park | | > |
| Challenge Cup 1964/65 | Round 2 | 27 | Workington | 18 | Halifax | 5 | Derwent Park | | > |
| Challenge Cup 1964/65 | Round 3 | Mar 13 | Workington | 4 | Wigan | 10 | Derwent Park | | > |
| Challenge Cup 1965/66 | Round 2 | Mar 19 | Workington | 5 | Hull KR | 7 | Derwent Park | | > |
| Challenge Cup 1967/68 | Round 1 | Feb 8 | Workington | 5 | Whitehaven | 2 | Derwent Park | | > |
| Challenge Cup 1967/68 | Round 2 | 24 | Workington | 2 | Castleford | 7 | Derwent Park | | > |
| Challenge Cup 1968/69 | Round 1 | Jan 25 | Workington | 5 | Swinton | 2 | Derwent Park | | > |
| Challenge Cup 1969/70 | Round 1 | Feb 7 | Workington | 6 | Leigh | 17 | Derwent Park | | > |
| Challenge Cup 1970/71 | Round 1 | Jan 23 | Workington | 6 | St Helens | 8 | Derwent Park | | > |
| Challenge Cup 1972/73 | Round 2 | Feb 17 | Workington | 8 | Dewsbury | 10 | Derwent Park | | > |
| Challenge Cup 1973/74 | Round 1 | Feb 2 | Workington | 14 | York | 4 | Derwent Park | | > |
| Challenge Cup 1973/74 | Round 2 | 24 | Workington | 4 | Dewsbury | 14 | Derwent Park | | > |
| Challenge Cup 1974/75 | Round 1 | Feb 12 | Workington | 14 | Barrow | 3 | Derwent Park | | > |
| Challenge Cup 1975/76 | Round 1 | Feb 15 | Workington | 10 | Swinton | 7 | Derwent Park | | > |
| Challenge Cup 1976/77 | Round 2 | Feb 27 | Workington | 13 | Salford | 4 | Derwent Park | | > |
| Challenge Cup 1976/77 | Round 3 | Mar 13 | Workington | 2 | Leeds | 8 | Derwent Park | | > |
| Challenge Cup 1977/78 | Round 1 | Feb 26 | Workington | 16 | Keighley | 5 | Derwent Park | | > |
| Challenge Cup 1977/78 | Round 2 | Mar 12 | Workington | 8 | Castleford | 8 | Derwent Park | | > |
| Challenge Cup 1980/81 | Round 1 | Feb 15 | Workington | 17 | Rochdale | 8 | Derwent Park | 2,459 | > |
| Challenge Cup 1981/82 | Round 1 | Feb 13 | Workington | 32 | Blackpool | 8 | Derwent Park | 1,410 | > |
| Challenge Cup 1982/83 | Round 2 | Feb 27 | Workington | 14 | Swinton | 9 | Derwent Park | 1,751 | > |
| Challenge Cup 1982/83 | Round 3 | Mar 13 | Workington | 0 | Bradford | 17 | Derwent Park | 3,894 | > |
| Challenge Cup 1983/84 | Round 2 | Feb 26 | Workington | 3 | Leeds | 12 | Derwent Park | 4,110 | > |
| Challenge Cup 1984/85 | Round 1 | Feb 17 | Workington | 28 | Dewsbury | 6 | Derwent Park | 858 | > |
| Challenge Cup 1990/91 | Prelim Round | Jan 27 | Hensingham | 7 | Dewsbury | 24 | Derwent Park | | > |
| Challenge Cup 1990/91 | Round 1 | Feb 17 | Workington | 18 | Hull KR | 12 | Derwent Park | 3,380 | > |
| Challenge Cup 1990/91 | Round 2 | 24 | Workington | 15 | Oldham | 20 | Derwent Park | 5,549 | > |
| Challenge Cup 1991/92 | Prelim Round | Jan 13 | Workington | 11 | Carlisle | 4 | Derwent Park | 2,695 | > |
| Challenge Cup 1991/92 | Round 1 | 26 | Workington | 13 | Wakefield | 8 | Derwent Park | 2,837 | > |
| Challenge Cup 1991/92 | Round 2 | Feb 9 | Workington | 9 | London | 2 | Derwent Park | 2,656 | > |
| Challenge Cup 1991/92 | Round 3 | 23 | Workington | 8 | Hull | 24 | Derwent Park | 5,298 | > |
| Challenge Cup 1993/94 | Round 2 | Dec 18 | Hensingham | 40 | Myson | 0 | Derwent Park | | > |
| Challenge Cup 1993/94 | Round 3 | Jan 16 | Workington | 24 | Beverley | 10 | Derwent Park | 1,277 | > |
| Challenge Cup 1993/94 | Round 5 | Feb 13 | Workington | 0 | Bradford | 32 | Derwent Park | 5,294 | > |
| Challenge Cup 1994/95 | Round 2 | Dec 31 | Hensingham | 8 | Heworth | 14 | Derwent Park | | > |
| Challenge Cup 1994/95 | Round 4 | Feb 12 | Workington | 30 | Hull | 6 | Derwent Park | 3,081 | > |
| Challenge Cup 1994/95 | Round 5 | 26 | Workington | 94 | Leigh | 4 | Derwent Park | 3,436 | > |
| Challenge Cup 1996 | Round 4 | Feb 11 | Workington | 10 | Widnes | 17 | Derwent Park | 2,339 | > |
| Challenge Cup 1997 | Round 3 | Jan 26 | Workington | 86 | Thatto Heath | 0 | Derwent Park | 1,228 | > |
| Challenge Cup 1997 | Round 4 | Feb 9 | Workington | 14 | Keighley | 24 | Derwent Park | 3,057 | > |
| Challenge Cup 1998 | Round 3 | Feb 1 | Workington | 12 | Haydock | 8 | Derwent Park | 1,139 | > |
| Challenge Cup 1998 | Round 4 | 15 | Ellenborough | 14 | Hunslet | 12 | Derwent Park | 1,338 | > |
| Challenge Cup 1999 | Round 3 | Jan 31 | Workington | 30 | Skirlaugh | 4 | Derwent Park | 1,316 | > |
| Challenge Cup 2000 | Round 3 | Jan 30 | Workington | 12 | Skirlaugh | 2 | Derwent Park | 599 | > |
| Challenge Cup 2001 | Round 3 | Jan 28 | Workington | 38 | Lock Lane | 0 | Derwent Park | 867 | > |
| Challenge Cup 2001 | Round 4 | Feb 11 | Workington | 6 | Wakefield Trinity | 56 | Derwent Park | 1,710 | > |
| Challenge Cup 2002 | Round 3 | Jan 27 | Workington | 38 | Toulouse | 12 | Derwent Park | 954 | > |
| Challenge Cup 2002 | Round 3 | 30 | Ellenborough | 6 | Hull KR | 38 | Derwent Park | 596 | > |
| Challenge Cup 2002 | Round 5 | Feb 24 | Workington | 12 | Halifax | 32 | Derwent Park | 2,109 | > |
| Challenge Cup 2004 | Round 4 | Feb 29 | Workington | 18 | Leeds | 68 | Derwent Park | 4,829 | > |
| Challenge Cup 2005 | Round 3 | Mar 13 | Workington | 44 | Wigan St Judes | 20 | Derwent Park | 899 | > |
| Challenge Cup 2007 | Round 3 | Mar 11 | Workington | 18 | Oulton | 10 | Derwent Park | 529 | > |
| Challenge Cup 2008 | Round 3 | Mar 8 | Wigan St Pats | 14 | Workington | 50 | Derwent Park | 333 | > |
| Challenge Cup 2008 | Round 4 | Apr 20 | Workington | 12 | Hull KR | 68 | Derwent Park | 1,227 | > |
| Challenge Cup 2009 | Round 3 | Mar 7 | Workington | 6 | Lézignan | 18 | Derwent Park | 314 | > |
| Challenge Cup 2012 | Round 3 | Mar 25 | Workington | 6 | Batley | 22 | Derwent Park | 601 | > |
| Challenge Cup 2013 | Round 3 | Apr 7 | Workington | 24 | Carcassonne | 16 | Derwent Park | 598 | > |
| Challenge Cup 2013 | Round 5 | May 12 | Workington | 0 | Widnes | 36 | Derwent Park | 1,657 | > |
| Challenge Cup 2018 | Round 4 | Mar 18 | Workington | 20 | London | 22 | Derwent Park | 548 | > |
| Challenge Cup 2019 | Round 3 | Mar 17 | Workington | 22 | Siddal | 0 | Derwent Park | 355 | > |
| Challenge Cup 2019 | Round 4 | 31 | Workington | 21 | Newcastle | 20 | Derwent Park | 590 | > |
| Challenge Cup 2020 | Round 3 | Feb 16 | Workington | 28 | West Bowling | 22 | Derwent Park | 950 | > |
| Challenge Cup 2020 | Round 4 | 23 | Workington | 22 | Doncaster | 12 | Derwent Park | 612 | > |
| Challenge Cup 2022 | Round 4 | Feb 27 | Workington | 26 | Dewsbury | 12 | Derwent Park | 872 | > |
| Challenge Cup 2023 | Round 2 | Feb 26 | Workington | 68 | Wigan Rose Bridge | 6 | Derwent Park | 603 | > |
| Challenge Cup 2025 | Round 3 | Feb 7 | Workington | 0 | Leigh | 60 | Fibrus Community Stadium | | > |
| Challenge Cup 2026 | Round 3 | Feb 6 | Workington | 2 | St Helens | 98 | Fibrus Community Stadium | 4,169 | > |
79 games
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