Thatto Heath| 18 | | Craven Park | | > | | Challenge Cup - Prelim Round
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| Sun | 15 Jan 1989 | Leeds | 32 | Hunslet | 6 | R. Tennant | Headingley | 9,090 | > |
| Sun | 15 Jan 1989 | Milford Amateurs | 0 | Swinton | 36 | | McLaren | | > |
| Sun | 15 Jan 1989 | Wakefield T. | 18 | Bramley | 10 | J. Holdsworth | Belle Vue | 2,855 | > |
| Sun | 15 Jan 1989 | West Hull | 2 | Doncaster | 48 | | Boulevard | | > |
| Sun | 15 Jan 1989 | York | 35 | Workington | 8 | K. Allatt | Wigginton Rd | 1,959 | > |
| Challenge Cup - Round 1
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| Sat | 28 Jan 1989 | Hull | 4 | Castleford | 7 | S. Haigh | Boulevard | 9,194 | > |
| Sun | 29 Jan 1989 | Barrow | 38 | Huddersfield | 16 | B. Galtress | Craven Park | 1,859 | > |
| Sun | 29 Jan 1989 | Carlisle | 58 | Mansfield | 1 | K. Spencer | Gillford Park | 663 | > |
| Sun | 29 Jan 1989 | Chorley B. | 8 | Thatto Heath | 4 | J. Whitelam | Victory Park | 736 | > |
| Sun | 29 Jan 1989 | Dewsbury | 9 | Oldham | 40 | K. Dockray | Crown Flatt | 2,356 | > |
| Sun | 29 Jan 1989 | Doncaster | 6 | Wigan | 38 | D. Carter | Tattersfield | 5,274 | > |
| Sun | 29 Jan 1989 | Fulham | 10 | Bradford N. | 28 | J. Smith | Polytechnic | 1,487 | > |
| Sun | 29 Jan 1989 | Rochdale H. | 24 | Hull KR | 28 | G. Kershaw | Spotland | 1,625 | > |
| Sun | 29 Jan 1989 | Runcorn H. | 10 | Keighley | 28 | G. Holgate | Canal St | 428 | > |
| Sun | 29 Jan 1989 | Salford | 14 | Widnes | 18 | J. Kendrew | The Willows | 7,094 | > |
| Sun | 29 Jan 1989 | Sheffield | 23 | Leigh | 17 | R. Whitfield | Owlerton | 1,898 | > |
| Sun | 29 Jan 1989 | Swinton | 5 | St Helens | 16 | S. Cross | Station Road | 5,317 | > |
| Sun | 29 Jan 1989 | Wakefield T. | 34 | Batley | 4 | P. Houghton | Belle Vue | 2,895 | > |
| Sun | 29 Jan 1989 | Warrington | 25 | Halifax | 8 | J. Holdsworth | Wilderspool | 6,209 | > |
| Sun | 29 Jan 1989 | Whitehaven | 0 | Featherstone R. | 32 | B. Simpson | Recreation Gnd | 2,729 | > |
| Sun | 29 Jan 1989 | York | 9 | Leeds | 28 | R. Tennant | Bootham Crescent | 11,347 | > |
| Challenge Cup - Round 2
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| Sat | 11 Feb 1989 | Castleford | 18 | Widnes | 32 | S. Cross | Wheldon Road | 10,765 | > |
| Sun | 12 Feb 1989 | Bradford N. | 4 | Wigan | 17 | R. Whitfield | Odsal | 16,738 | > |
| Sun | 12 Feb 1989 | Hull KR | 28 | Chorley B. | 4 | B. Simpson | Craven Park | 3,471 | > |
| Sun | 12 Feb 1989 | Leeds | 24 | Carlisle | 4 | C. Steele | Headingley | 9,484 | > |
| Sun | 12 Feb 1989 | St Helens | 28 | Barrow | 6 | J. Kendrew | Knowsley | 8,661 | > |
| Sun | 12 Feb 1989 | Sheffield | 20 | Oldham | 32 | J. Holdsworth | Owlerton | 3,636 | > |
| Sun | 12 Feb 1989 | Wakefield T. | 4 | Featherstone R. | 10 | D. Carter | Belle Vue | 7,695 | > |
| Sun | 12 Feb 1989 | Warrington | 56 | Keighley | 7 | S. Haigh | Wilderspool | 4,184 | > |
| Challenge Cup - Round 3
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| Sat | 25 Feb 1989 | Oldham | 4 | Wigan | 12 | D. Carter | Watersheddings | 9,402 | > |
| Sun | 26 Feb 1989 | Hull KR | 4 | Warrington | 30 | R. Tennant | Craven Park | 7,283 | > |
| Sun | 26 Feb 1989 | Leeds | 4 | Widnes | 24 | J. Holdsworth | Headingley | 26,303 | > |
| Sun | 26 Feb 1989 | St Helens | 32 | Featherstone R. | 3 | R. Whitfield | Knowsley | 11,063 | > |
| Challenge Cup - Semi Final
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| Sat | 11 Mar 1989 | St Helens | 16 | Widnes | 14 | J. Holdsworth | Central Park | 17,119 | > |
| Sat | 25 Mar 1989 | Wigan | 13 | Warrington | 6 | R. Whitfield | Maine Road | 26,529 | > |
| Challenge Cup - Final
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| Sat | 29 Apr 1989 | Wigan | 27 | St Helens | 0 | R. Tennant | Wembley | 78,000 | > |