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The Challenge Cup semi final is played to determine the teams who play in the Challenge Cup final.
| * | Match went to extra time |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 1897 | 1 |  Batley | 6-0 |  Warrington | Fartown |
| 2 |  St. Helens | 7-0 |  Swinton | Wheater's Field |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 1980 | 1 |  Hull Kingston Rovers | 20-7 |  Halifax | |
| 2 |  Hull F.C. | 10-5 |  Widnes | ||
| 1981 | 1 | Widnes | 17-9 | Warrington | Central Park |
| 2 | Hull Kingston Rovers | 22-5 | St. Helens | Headingley | |
| 1982 | 1 | Hull | 15-11 |  Castleford | Headingley |
| 2 | Widnes | 11-8 |  Leeds | Station Road | |
| 1983 | 1 |  Featherstone Rovers | 11-6 |  Bradford Northern | Headingley |
| 2 | Hull | 14-7 | Castleford | Elland Road | |
| 1984 | 1 |  Wigan | 14-8 |  York | Elland Road |
| 2 | Widnes | 15-4 | Leeds | Station Road | |
| 1985 | 1 | Wigan | 18-11 | Hull Kingston Rovers | Central Park |
| 2 | Hull | 10-10 | Castleford | Headingley | |
| R | Hull | 22-16 | Castleford | Headingley | |
| 1986 | 1 | Castleford | 18-7 |  Oldham | Central Park |
| 2 | Hull Kingston Rovers | 24-24 | Leeds | Elland Road | |
| R | Hull Kingston Rovers | 17-0 | Leeds | Elland Road | |
| 1987 | 1 | St. Helens | 14-8 |  Leigh | Central Park |
| 2 | Halifax | 12-8 | Widnes | Headingley | |
| 1988 | 1 | Wigan | 18-7 |  Salford | Burnden Park |
| 2 | Halifax | 0-0 | Hull | Headingley | |
| R | Halifax | 4-3 | Hull | Elland Road | |
| 1989 | 1 | St. Helens | 16-14 | Widnes | Central Park |
| 2 | Wigan | 13-6 | Warrington | Maine Road |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 1990 | 1 | Wigan | 20-14 | St. Helens | Old Trafford |
| 2 | Warrington | 10-6 | Oldham | Central Park | |
| 1991 | 1 | Wigan | 30-16 | Oldham | Burnden Park |
| 2 | St. Helens | 19-2 | Widnes | Central Park | |
| 1992 | 1 | Castleford | 8-4 | Hull | Headingley |
| 2 | Wigan | 71-10 | Bradford Northern | Burnden Park | |
| 1993 | 1 | Widnes | 39-4 | Leeds | Central Park |
| 2 | Wigan | 15-6 | Bradford Northern | Elland Road | |
| 1994 | 1 | Wigan | 20-6 | Castleford | Headingley |
| 2 | Leeds | 20-8 | St. Helens | Central Park | |
| 1995 | 1 | Wigan | 48-20 | Oldham | Kirklees Stadium |
| 2 | Leeds | 39-2 | Featherstone Rovers | Elland Road | |
| 1996 | 1 | St. Helens | 24-14 | Widnes | Central Park |
| 2 | Bradford | 28-6 | Leeds | Kirklees Stadium | |
| 1997 | 1 | St. Helens | 50-20 | Salford | Central Park |
| 2 | Bradford | 24-10 | Leeds | Kirklees Stadium | |
| 1998 | 1 |  Sheffield Eagles | 22-18 | Salford | Headingley |
| 2 | Wigan | 38-8 |  London Broncos | Kirklees Stadium | |
| 1999 | 1 | London Broncos | 33-27 | Castleford | Headingley |
| 2 | Leeds | 38-10 | Bradford | Kirklees Stadium |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 2000 | 1 | Bradford | 44-20 | Warrington | Headingley |
| 2 | Leeds | 28-22 | Hull | Kirklees Stadium | |
| 2001 | 1 | St. Helens | 27-22 | Leeds | DW Stadium |
| 2 | Bradford | 39-22 | Warrington | Kirklees Stadium | |
| 2002 | 1 | Wigan | 20-10 | Castleford | Headingley |
| 2 | St. Helens | 42-16 | Leeds | DW Stadium | |
| 2003 | 1 | Bradford | 36-22 | Wigan | Kirklees Stadium |
| 2 | Leeds | 33-26 | St. Helens | Kirklees Stadium | |
| 2004 | 1 | Wigan | 30-18 | Warrington | Halton Stadium |
| 2 | St. Helens | 46-6 |  Huddersfield | Halliwell Jones Stadium | |
| 2005 | 1 | Hull | 34-8 | St. Helens | Kirklees Stadium |
| 2 | Leeds | 56-18 |  Toulouse | Kirklees Stadium | |
| 2006 | 1 | St. Helens | 50-0 | Hull Kingston Rovers | Kirklees Stadium |
| 2 | Huddersfield | 30-12 | Leeds | Odsal | |
| 2007 | 1 | St. Helens | 35-14 | Bradford | Kirklees Stadium |
| 2 |  Catalans Dragons | 37-24 | Wigan | Halliwell Jones Stadium | |
| 2008 | 1 | St. Helens | 26-16 | Leeds | Kirklees Stadium |
| 2 | Hull | 32-24 |  Wakefield Trinity | Keepmoat Stadium | |
| 2009 | 1 | Warrington | 39-26 | Wigan | Halton Stadium |
| 2 | Huddersfield | 24-14 | St. Helens | Halliwell Jones Stadium |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 2010 | 1 | Leeds | 32-28 | St. Helens | Kirklees Stadium |
| 2 | Warrington | 54-12 | Catalans Dragons | Halton Stadium | |
| 2011 | 1 | Wigan | 18-12 | St. Helens | Halliwell Jones Stadium |
| 2 | Leeds | 10-8* | Castleford | Keepmoat Stadium | |
| 2012 | 1 | Leeds | 39-28 | Wigan | Kirklees Stadium |
| 2 | Warrington | 33-6 | Huddersfield | Salford City Stadium | |
| 2013 | 1 | Wigan | 70-0 | London | Leigh Sports Village |
| 2 | Hull | 16-12 | Warrington | Kirklees Stadium | |
| 2014 | 1 | Leeds | 24-16 | Warrington | Langtree Park |
| 2 | Castleford | 22-6 | Widnes | Leigh Sports Village | |
| 2015 | 1 | Leeds | 24-14 | St. Helens | Halliwell Jones Stadium |
| 2 | Hull Kingston Rovers | 26-18 | Warrington | Headingley | |
| 2016 | 1 | Hull | 16-12 | Wigan | Keepmoat Stadium |
| 2 | Warrington | 56-12 | Wakefield Trinity | Leigh Sports Village | |
| 2017 | 1 | Hull | 43-24 | Leeds | Keepmoat Stadium |
| 2 | Wigan | 27-14 | Salford | Halliwell Jones Stadium | |
| 2018 | 1 | St. Helens | 16-35 | Catalans | University of Bolton Stadium |
| 2 | Warrington | 48-12 | Leeds | ||
| 2019 | 1 | St. Helens | 26-2 | Halifax | University of Bolton Stadium |
| 2 | Warrington | 22-14 | Hull |
| Year | SF | Winner | Score | Loser | Venue |
|---|---|---|---|---|---|
| 2020 | 1 | Leeds | 26-12 | Wigan | Totally Wicked Stadium |
| 2 | Salford | 24-22 | Warrington | ||
| 2021 | 1 | St Helens | 26-12 | Hull F.C. | Leigh Sports Village |
| 2 | Castleford | 35-20 | Warrington | ||
| 2022 | 1 | Wigan | 20-18 | St Helens | Elland Road |
| 2 | Huddersfield | 25-4 | Hull Kingston Rovers | ||
| 2023 | 1 | Leigh | 12-10 | St Helens | Halliwell Jones Stadium |
| 2 | Hull Kingston Rovers | 11-10* | Wigan | Headingley |
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