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| Competition | Round | Date | Home | | Away | | Venue | Crowd | |
|---|
| Challenge Cup 1900/01 | Round 1 | Mar 2 | Whitehaven Recs | 0 | Widnes | 3 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1901/02 | Round 2 | Mar 26 | Whitehaven Recs | 6 | Idle | 3 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1906/07 | Round 1 | Mar 16 | Whitehaven Recs | 10 | Saville Green | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1906/07 | Round 2 | 23 | Whitehaven Recs | 0 | Keighley | 14 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1907/08 | Round 1 | Feb 29 | Whitehaven Recs | 13 | St Helens | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1927/28 | Round 1 | Feb 11 | Whitehaven Recs | 0 | Swinton | 44 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1945/46 | Round 1 | Feb 9 | Kells | 0 | Warrington | 3 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1948/49 | Rd. 1 (1st Leg) | Feb 12 | Whitehaven | 0 | Keighley | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1949/50 | Round 1 | Feb 11 | Whitehaven | 12 | Belle Vue Rangers | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1950/51 | Round 1 | Feb 10 | Whitehaven | 2 | Huddersfield | 7 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1950/51 | Round 1 | 17 | Broughton Moor | 0 | Batley | 36 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1951/52 | Round 1 | Feb 9 | Whitehaven | 16 | Rylands Recs | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1951/52 | Round 2 | Mar 1 | Whitehaven | 7 | Halifax | 5 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1951/52 | Round 3 | 15 | Whitehaven | 2 | Barrow | 10 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1952/53 | Round 1 | Feb 7 | Whitehaven | 13 | Hull | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1953/54 | Round 1 | Feb 13 | Whitehaven | 15 | Wakefield | 3 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1956/57 | Round 1 | Feb 9 | Whitehaven | 9 | St Helens | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1956/57 | Round 2 | 23 | Whitehaven | 7 | Hunslet | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1956/57 | Round 3 | Mar 9 | Whitehaven | 2 | Widnes | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1958/59 | Round 1 | Feb 21 | Whitehaven | 25 | Liverpool | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1958/59 | Round 2 | Mar 7 | Whitehaven | 2 | Halifax | 7 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1959/60 | Round 3 | Mar 19 | Whitehaven | 10 | Wakefield | 21 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1960/61 | Round 1 | Feb 11 | Whitehaven | 8 | Blackpool | 3 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1963/64 | Round 1 | Feb 8 | Whitehaven | 7 | Hull | 4 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1963/64 | Round 2 | 29 | Whitehaven | 5 | Castleford | 29 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1966/67 | Round 1 | Feb 4 | Whitehaven | 2 | Barrow | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1969/70 | Round 1 | Feb 7 | Whitehaven | 4 | Warrington | 20 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1970/71 | Round 1 | Jan 23 | Whitehaven | 0 | Castleford | 15 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1971/72 | Round 1 | Jan 29 | Whitehaven | 0 | Castleford | 17 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1973/74 | Round 1 | Feb 3 | Whitehaven | 5 | Bramley | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1974/75 | Round 1 | Feb 8 | Whitehaven | 7 | Leeds | 16 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1976/77 | Round 1 | Feb 13 | Whitehaven | 5 | Featherstone | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1977/78 | Round 1 | Feb 26 | Whitehaven | 13 | Wakefield | 21 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1981/82 | Round 1 | Feb 14 | Whitehaven | 7 | Hull KR | 17 | Recreation Ground (Whitehaven) | 3,965 | > |
| Challenge Cup 1983/84 | Round 1 | Feb 12 | Whitehaven | 10 | Fulham | 17 | Recreation Ground (Whitehaven) | 1,683 | > |
| Challenge Cup 1984/85 | Round 1 | Feb 24 | Whitehaven | 8 | Wakefield | 10 | Recreation Ground (Whitehaven) | 1,907 | > |
| Challenge Cup 1986/87 | Prelim Round | Jan 22 | Kells | 4 | Fulham | 4 | Recreation Ground (Whitehaven) | 2,310 | > |
| Challenge Cup 1987/88 | Prelim Round | Jan 13 | Kells | 0 | Leeds | 28 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1987/88 | Prelim Round | 20 | Whitehaven | 8 | Carlisle | 22 | Recreation Ground (Whitehaven) | 2,614 | > |
| Challenge Cup 1988/89 | Round 1 | Jan 29 | Whitehaven | 0 | Featherstone | 32 | Recreation Ground (Whitehaven) | 2,729 | > |
| Challenge Cup 1989/90 | Round 1 | Jan 28 | Whitehaven | 23 | Leigh | 22 | Recreation Ground (Whitehaven) | 1,528 | > |
| Challenge Cup 1989/90 | Round 2 | Feb 11 | Whitehaven | 46 | Keighley | 10 | Recreation Ground (Whitehaven) | 1,653 | > |
| Challenge Cup 1991/92 | Qualifier | Jan 12 | Kells | 17 | Hull Dockers | 14 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1991/92 | Round 1 | 28 | Whitehaven | 4 | Sheffield | 56 | Recreation Ground (Whitehaven) | 852 | > |
| Challenge Cup 1991/92 | Round 1 | 29 | Kells | 14 | Hunslet | 32 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1992/93 | Round 1 | Jan 31 | Whitehaven | 8 | Widnes | 20 | Recreation Ground (Whitehaven) | 3,791 | > |
| Challenge Cup 1993/94 | Round 1 | Dec 4 | Egremont | 28 | Ace Amateurs | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1993/94 | Round 3 | Jan 16 | Whitehaven | 44 | West Hull | 4 | Recreation Ground (Whitehaven) | 718 | > |
| Challenge Cup 1993/94 | Round 5 | Feb 13 | Whitehaven | 4 | St Helens | 46 | Recreation Ground (Whitehaven) | 4,161 | > |
| Challenge Cup 1994/95 | Round 1 | Dec 10 | Egremont | 34 | New Earswick | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1994/95 | Round 3 | Jan 22 | Whitehaven | 64 | Moorends | 12 | Recreation Ground (Whitehaven) | 637 | > |
| Challenge Cup 1994/95 | Round 4 | Feb 12 | Whitehaven | 24 | Wakefield | 12 | Recreation Ground (Whitehaven) | 2,092 | > |
| Challenge Cup 1994/95 | Quarter Final | Mar 12 | Whitehaven | 14 | Featherstone | 42 | Recreation Ground (Whitehaven) | 4,119 | > |
| Challenge Cup 1996 | Round 1 | Dec 2 | Egremont | 12 | Hensingham | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1996 | Round 2 | 16 | Woolston | 20 | Egremont | 20 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1996 | Round 2 | 31 | Egremont | 13 | Woolston | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1996 | Round 4 | Feb 11 | Whitehaven | 6 | Halifax | 18 | Recreation Ground (Whitehaven) | 1,619 | > |
| Challenge Cup 1997 | Round 1 | Dec 21 | Egremont | 32 | Folly Lane | 14 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1997 | Round 3 | Jan 26 | Whitehaven | 12 | Skirlaugh | 6 | Recreation Ground (Whitehaven) | 875 | > |
| Challenge Cup 1997 | Round 4 | Feb 9 | Whitehaven | 8 | Leeds | 48 | Recreation Ground (Whitehaven) | 2,321 | > |
| Challenge Cup 1998 | Round 2 | Dec 20 | Egremont | 24 | Hull Dockers | 12 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1998 | Round 3 | Feb 1 | Whitehaven | 48 | Lock Lane | 7 | Recreation Ground (Whitehaven) | 830 | > |
| Challenge Cup 1998 | Round 4 | 13 | Egremont | 18 | Workington | 0 | Recreation Ground (Whitehaven) | 3,054 | > |
| Challenge Cup 1998 | Round 4 | 15 | Whitehaven | 12 | Hull | 26 | Recreation Ground (Whitehaven) | 2,030 | > |
| Challenge Cup 1999 | Round 2 | Jan 2 | Egremont | 21 | Haydock | 0 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 1999 | Round 3 | 31 | Whitehaven | 22 | Saddleworth | 6 | Recreation Ground (Whitehaven) | 779 | > |
| Challenge Cup 1999 | Round 4 | Feb 14 | Whitehaven | 24 | Lancashire | 6 | Recreation Ground (Whitehaven) | 827 | > |
| Challenge Cup 1999 | Round 5 | 28 | Whitehaven | 18 | Oldham | 2 | Recreation Ground (Whitehaven) | 1,438 | > |
| Challenge Cup 2000 | Round 3 | Jan 30 | Whitehaven | 42 | Shaw Cross | 0 | Recreation Ground (Whitehaven) | 503 | > |
| Challenge Cup 2001 | Round 3 | Jan 28 | Whitehaven | 34 | Oldham St Annes | 16 | Recreation Ground (Whitehaven) | 616 | > |
| Challenge Cup 2001 | Round 5 | Feb 25 | Whitehaven | 22 | St Helens | 34 | Recreation Ground (Whitehaven) | 4,750 | > |
| Challenge Cup 2002 | Round 3 | Jan 27 | Whitehaven | 50 | Dewsbury Celtic | 0 | Recreation Ground (Whitehaven) | 757 | > |
| Challenge Cup 2002 | Round 4 | Feb 10 | Whitehaven | 16 | Dewsbury | 8 | Recreation Ground (Whitehaven) | 938 | > |
| Challenge Cup 2003 | Round 3 | Jan 24 | Wath Brow Hornets | 13 | Workington | 12 | Recreation Ground (Whitehaven) | 3,017 | > |
| Challenge Cup 2003 | Round 3 | 26 | Whitehaven | 66 | Cott. Phoenix | 6 | Recreation Ground (Whitehaven) | 1,001 | > |
| Challenge Cup 2003 | Round 4 | Feb 8 | Wath Brow Hornets | 6 | Batley | 18 | Recreation Ground (Whitehaven) | 1,333 | > |
| Challenge Cup 2004 | Quarter Final | Mar 28 | Whitehaven | 10 | Warrington | 42 | Recreation Ground (Whitehaven) | 5,328 | > |
| Challenge Cup 2005 | Round 3 | Mar 12 | Wath Brow Hornets | 32 | Dewsbury | 30 | Recreation Ground (Whitehaven) | 741 | > |
| Challenge Cup 2005 | Round 3 | 13 | Oldham St Annes | 30 | Whitehaven | 62 | Recreation Ground (Whitehaven) | 968 | > |
| Challenge Cup 2006 | Round 3 | Mar 10 | Whitehaven | 72 | Pia | 0 | Recreation Ground (Whitehaven) | 2,300 | > |
| Challenge Cup 2006 | Round 3 | 15 | Kells | 6 | Halifax | 26 | Recreation Ground (Whitehaven) | 743 | > |
| Challenge Cup 2007 | Round 1 | Feb 3 | Egremont | 34 | Oldham St Annes | 18 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2007 | Round 3 | Mar 11 | Whitehaven | 24 | Doncaster | 10 | Recreation Ground (Whitehaven) | 1,268 | > |
| Challenge Cup 2007 | Round 4 | Apr 1 | Whitehaven | 36 | Halifax | 8 | Recreation Ground (Whitehaven) | 2,128 | > |
| Challenge Cup 2007 | Round 5 | May 13 | Whitehaven | 14 | Catalans | 24 | Recreation Ground (Whitehaven) | 3,008 | > |
| Challenge Cup 2008 | Round 3 | Mar 9 | Wath Brow Hornets | 14 | Swinton | 40 | Recreation Ground (Whitehaven) | 631 | > |
| Challenge Cup 2008 | Round 4 | Apr 18 | Whitehaven | 46 | Lézignan | 6 | Recreation Ground (Whitehaven) | 1,250 | > |
| Challenge Cup 2009 | Round 1 | Jan 24 | Egremont | 0 | Wath Brow Hornets | 42 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2009 | Round 1 | 24 | Kells | 26 | Eastmoor | 14 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2009 | Round 2 | Feb 16 | Kells | 31 | Leigh Miners R. | 22 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2009 | Round 3 | Mar 8 | Wath Brow Hornets | 14 | London | 12 | Recreation Ground (Whitehaven) | 320 | > |
| Challenge Cup 2009 | Round 3 | 14 | Kells | 12 | Hunslet | 22 | Recreation Ground (Whitehaven) | 251 | > |
| Challenge Cup 2011 | Round 2 | Feb 5 | Egremont | 22 | Wath Brow Hornets | 10 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2011 | Round 1 | 12 | Kells | 14 | Dudley Hill | 22 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2011 | Round 3 | Mar 5 | Whitehaven | 14 | Lézignan | 27 | Recreation Ground (Whitehaven) | 651 | > |
| Challenge Cup 2012 | Qualifier | Feb 11 | Egremont | 22 | Bank Quay | 16 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Qualifier | 11 | Kells | 20 | Widnes W Bank | 18 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Qualifier | 12 | Blackbrook | 18 | Eccles | 8 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Round 1 | 18 | Egremont | 30 | Leeds Met Uni | 6 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Round 1 | 25 | Blackbrook | 24 | East Leeds | 20 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Round 1 | 25 | Kells | 34 | Normanton | 12 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Round 2 | Mar 10 | Egremont | 32 | Wigan Rose Bridge | 22 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2012 | Round 3 | 23 | Egremont | 14 | Oldham | 22 | Recreation Ground (Whitehaven) | 468 | > |
| Challenge Cup 2012 | Round 3 | 24 | Wath Brow Hornets | 22 | South Wales | 24 | Recreation Ground (Whitehaven) | 350 | > |
| Challenge Cup 2012 | Round 3 | 25 | Whitehaven | 52 | Hunslet Warriors | 6 | Recreation Ground (Whitehaven) | 534 | > |
| Challenge Cup 2012 | Round 4 | Apr 15 | Whitehaven | 18 | Salford | 58 | Recreation Ground (Whitehaven) | 751 | > |
| Challenge Cup 2013 | Round 3 | Apr 7 | Whitehaven | 38 | London | 32 | Recreation Ground (Whitehaven) | 440 | > |
| Challenge Cup 2013 | Round 4 | 21 | Whitehaven | 12 | Workington | 16 | Recreation Ground (Whitehaven) | 1,320 | > |
| Challenge Cup 2014 | Round 1 | Feb 1 | Kells | 24 | Wigan St Judes | 16 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2014 | Round 2 | 22 | Kells | 26 | Leigh Miners R. | 12 | Recreation Ground (Whitehaven) | | > |
| Challenge Cup 2015 | Round 3 | Mar 7 | Kells | 12 | Rochdale | 29 | Recreation Ground (Whitehaven) | 587 | > |
| Challenge Cup 2015 | Round 4 | 21 | Whitehaven | 12 | Featherstone | 36 | Recreation Ground (Whitehaven) | 525 | > |
| Challenge Cup 2017 | Round 4 | Mar 26 | Whitehaven | 46 | Oxford | 14 | Recreation Ground (Whitehaven) | 375 | > |
| Challenge Cup 2017 | Round 5 | Apr 23 | Whitehaven | 12 | Halifax | 36 | Recreation Ground (Whitehaven) | 636 | > |
| Challenge Cup 2018 | Round 3 | Feb 24 | Whitehaven | 16 | London | 14 | Recreation Ground (Whitehaven) | 439 | > |
| Challenge Cup 2018 | Round 4 | Mar 16 | Kells | 6 | Toronto Wolfpack | 56 | Recreation Ground (Whitehaven) | 1,000 | > |
| Challenge Cup 2018 | Round 4 | 18 | Whitehaven | 25 | Dewsbury | 18 | Recreation Ground (Whitehaven) | 414 | > |
| Challenge Cup 2018 | Round 5 | Apr 22 | Whitehaven | 38 | Rochdale | 0 | Recreation Ground (Whitehaven) | 604 | > |
| Challenge Cup 2019 | Round 3 | Mar 10 | Whitehaven | 74 | Wigan St Pats | 4 | Recreation Ground (Whitehaven) | 464 | > |
| Challenge Cup 2019 | Round 4 | 31 | Whitehaven | 21 | Rochdale | 22 | Recreation Ground (Whitehaven) | 889 | > |
| Challenge Cup 2020 | Round 4 | Mar 11 | Whitehaven | 16 | Dewsbury | 22 | Recreation Ground (Whitehaven) | 427 | > |
| Challenge Cup 2021 | Round 1 | Mar 20 | Whitehaven | 23 | Dewsbury | 16 | Recreation Ground (Whitehaven) | 0 | > |
| Challenge Cup 2022 | Round 5 | Mar 13 | Whitehaven | 38 | York City | 12 | LEL Arena | 798 | > |
| Challenge Cup 2022 | Round 6 | 26 | Whitehaven | 4 | St Helens | 46 | LEL Arena | 4,869 | > |
| Challenge Cup 2025 | Round 2 | Jan 25 | Whitehaven | 24 | Swinton | 12 | The Ortus REC | 908 | > |
| Challenge Cup 2025 | Round 3 | Feb 8 | Whitehaven | 4 | Warrington | 44 | The Ortus REC | 3,980 | > |
