Batley| 45 | | Knowsley | | > | | Challenge Cup - Qualifier
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| Sat | 13 Jan 1990 | Millom | 0 | Bisons | 4 | | Devonshire Road | | > |
| Challenge Cup - Prelim Round
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| Sun | 14 Jan 1990 | Fulham | 23 | Doncaster | 16 | A. Burke | Polytechnic | 898 | > |
| Sun | 14 Jan 1990 | Leeds | 8 | Bradford N. | 24 | C. Morris | Headingley | 14,152 | > |
| Sun | 14 Jan 1990 | Oldham | 30 | Huddersfield | 8 | J. Kendrew | Watersheddings | 4,593 | > |
| Sun | 14 Jan 1990 | St Helens | 39 | Castleford | 12 | A. Bowman | Knowsley | 8,662 | > |
| Challenge Cup - Round 1
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| Sat | 27 Jan 1990 | Warrington | 20 | Featherstone R. | 12 | A. Bowman | Wilderspool | 3,435 | > |
| Sun | 28 Jan 1990 | Barrow | 12 | Sheffield | 22 | R. Whitfield | Craven Park | | > |
| Sun | 28 Jan 1990 | Bramley | 14 | St Helens | 22 | C. Tidball | McLaren | 2,710 | > |
| Sun | 28 Jan 1990 | Fulham | 14 | Ryedale-York | 14 | K. Allatt | Polytechnic | 856 | > |
| Sun | 28 Jan 1990 | Hull KR | 4 | Wigan | 6 | R. Tennant | Craven Park | 8,473 | > |
| Sun | 28 Jan 1990 | Hull | 46 | Halifax | 0 | J. Kendrew | Boulevard | 7,574 | > |
| Sun | 28 Jan 1990 | Nottingham | 2 | Dewsbury | 32 | S. Cross | Harvey Hadden | 529 | > |
| Sun | 28 Jan 1990 | Oldham | 30 | Workington | 8 | B. Simpson | Watersheddings | 3,710 | > |
| Sun | 28 Jan 1990 | Runcorn H. | 12 | Bradford N. | 22 | | Hoghton | | > |
| Sun | 28 Jan 1990 | Salford | 56 | Bisons | 6 | D. Asquith | The Willows | 1,935 | > |
| Sun | 28 Jan 1990 | Swinton | 10 | Wakefield T. | 10 | J. Whitelam | Station Road | 3,330 | > |
| Sun | 28 Jan 1990 | Trafford B. | 14 | Hunslet | 7 | F. Tickle | Springfield | 379 | > |
| Sun | 28 Jan 1990 | Whitehaven | 23 | Leigh | 22 | G. Kershaw | Recreation Gnd | 1,528 | > |
| Sun | 28 Jan 1990 | Widnes | 26 | Batley | 10 | J. Holdsworth | Naughton | 5,801 | > |
| Tue | 30 Jan 1990 | Chorley | 6 | Keighley | 12 | J. Smith | Victory Park | 552 | > |
| Tue | 30 Jan 1990 | Rochdale H. | 38 | Carlisle | 6 | K. Morris | Spotland | 1,609 | > |
| Wed | 31 Jan 1990 | Ryedale-York | 12 | Fulham | 16 | K. Allatt | Wigginton Rd | 2,059 | > |
| Wed | 31 Jan 1990 | Wakefield T. | 32 | Swinton | 4 | J. Whitelam | Belle Vue | 4,741 | > |
| Challenge Cup - Round 2
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| Sat | 10 Feb 1990 | Hull | 12 | St Helens | 24 | G. Kershaw | Boulevard | 8,066 | > |
| Sun | 11 Feb 1990 | Fulham | 2 | Bradford N. | 20 | J. Whitelam | Polytechnic | 1,685 | > |
| Sun | 11 Feb 1990 | Salford | 7 | Oldham | 18 | J. Holdsworth | The Willows | 6,472 | > |
| Sun | 11 Feb 1990 | Wakefield T. | 27 | Sheffield | 12 | C. Morris | Belle Vue | 5,359 | > |
| Sun | 11 Feb 1990 | Warrington | 20 | Trafford B. | 11 | P. Crashley | Wilderspool | 3,448 | > |
| Sun | 11 Feb 1990 | Whitehaven | 46 | Keighley | 10 | J. Kendrew | Recreation Gnd | 1,653 | > |
| Sun | 11 Feb 1990 | Widnes | 22 | Rochdale H. | 16 | A. Bowman | Naughton | 6,956 | > |
| Sun | 11 Feb 1990 | Wigan | 30 | Dewsbury | 6 | R. Campbell | Central Park | 11,113 | > |
| Challenge Cup - Round 3
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| Sat | 24 Feb 1990 | Wakefield T. | 14 | Wigan | 26 | R. Campbell | Belle Vue | 8,033 | > |
| Sun | 25 Feb 1990 | Bradford N. | 10 | Warrington | 12 | R. Whitfield | Odsal | 9,114 | > |
| Sun | 25 Feb 1990 | St Helens | 44 | Whitehaven | 10 | A. Bowman | Knowsley | 9,253 | > |
| Sun | 25 Feb 1990 | Widnes | 4 | Oldham | 16 | A. Bowman | Naughton | 11,802 | > |
| Challenge Cup - Semi Final
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| Sat | 10 Mar 1990 | Wigan | 20 | St Helens | 14 | R. Whitfield | Old Trafford | 26,489 | > |
| Sat | 31 Mar 1990 | Warrington | 10 | Oldham | 6 | J. Holdsworth | Central Park | 15,631 | > |
| Challenge Cup - Final
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| Sat | 28 Apr 1990 | Wigan | 36 | Warrington | 14 | J. Holdsworth | Wembley | 77,729 | > |