Uni of Wales Inst| 4 | | Ostley Bank | | > | | Sat | 05 Dec 1998 | Dudley Hill | 66 | Leeds Uni | 0 | | Neil Hunt Ground | | > |
| Sat | 05 Dec 1998 | Dewsbury Moor | 6 | Ellenborough | 40 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Eastmoor | 24 | Moldgreen | 34 | | King George's | | > |
| Sat | 05 Dec 1998 | Eccles | 78 | Garibaldi | 10 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Featherstone Lions | 34 | Queensbury | 26 | | Post Office Road | | > |
| Sat | 05 Dec 1998 | Hull Dockers | 23 | Park Amateurs | 6 | | Willows Sports | | > |
| Sat | 05 Dec 1998 | Ideal Isberg | 39 | Millom | 4 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Keighley Albion | 6 | Dodworth | 42 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Leigh East | 12 | Haydock | 18 | | [unknown] | | > |
| Sat | 05 Dec 1998 | London | 16 | Thatto Heath | 4 | | New River | | > |
| Sat | 05 Dec 1998 | Middleton | 12 | Wigan St Judes | 15 | | [unknown] | | > |
| Sat | 05 Dec 1998 | New Earswick | 14 | Townville | 16 | | White Rose Ave | | > |
| Sat | 05 Dec 1998 | Norland | 28 | Milford | 22 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Oulton | 42 | York Acorn | 8 | | Oulton Green | | > |
| Sat | 05 Dec 1998 | Queens | 20 | Redhill | 18 | | Bus. Vale | | > |
| Sat | 05 Dec 1998 | Shaw Cross | 12 | Featherstone MW | 16 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Siddal | 90 | Northside Saints | 10 | | [unknown] | | > |
| Sat | 05 Dec 1998 | Wigan Rose Bridge | 23 | Blackbrook | 16 | | [unknown] | | > |
| Sat | 12 Dec 1998 | Clayton | 10 | Normanton | 28 | | [unknown] | | > |
| Sat | 12 Dec 1998 | Gateshead P | 10 | Crosfields | 58 | | [unknown] | | > |
| Sat | 12 Dec 1998 | Ovenden | 22 | East Leeds | 14 | | Four Fields | | > |
| Sun | 13 Dec 1998 | Rochdale Mayfield | 36 | Leeds Met Uni | 18 | | Springhill | | > |
| Sun | 13 Dec 1998 | Scottish Eagles | 10 | Wath Brow Hornets | 34 | | [unknown] | | > |
| Challenge Cup - Round 2
|
|---|
| Sat | 19 Dec 1998 | Askam | 25 | Heworth | 22 | | Fallowfield Park | | > |
| Sat | 19 Dec 1998 | Beverley E Hull | 12 | Townville | 28 | | Eastmount | | > |
| Sat | 19 Dec 1998 | Dudley Hill | 29 | Wigan St Pats | 8 | | Neil Hunt Ground | | > |
| Sat | 19 Dec 1998 | Dodworth | 12 | Lock Lane | 24 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Eccles | 27 | Normanton | 16 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Moldgreen | 21 | Oulton | 18 | | Ridgeway | | > |
| Sat | 19 Dec 1998 | Norland | 39 | Crosfields | 0 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Oldham St Annes | 34 | Ellenborough | 6 | | Higginshaw Road | | > |
| Sat | 19 Dec 1998 | Queens | 28 | West Hull | 40 | | Bus. Vale | | > |
| Sat | 19 Dec 1998 | Rochdale Mayfield | 28 | Hull Dockers | 10 | | Springhill | | > |
| Sat | 19 Dec 1998 | Saddleworth | 10 | Walney | 6 | | Bank Road | | > |
| Sat | 19 Dec 1998 | Siddal | 27 | Featherstone MW | 7 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Skirlaugh | 8 | Ideal Isberg | 2 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Thornhill | 25 | Barrow Is. | 12 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Wath Brow Hornets | 16 | London | 6 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Wigan Rose Bridge | 6 | Leigh Miners R. | 17 | | [unknown] | | > |
| Sat | 19 Dec 1998 | Wigan St Judes | 32 | Woolston | 8 | | Parsons Meadow | | > |
| Sat | 02 Jan 1999 | Egremont | 21 | Haydock | 0 | | Recreation Gnd | | > |
| Sat | 02 Jan 1999 | Featherstone Lions | 37 | Ovenden | 18 | | Lionheart | | > |
| Challenge Cup - Round 3
|
|---|
| Sun | 31 Jan 1999 | Barrow | 44 | Dudley Hill | 16 | | Craven Park | 1,157 | > |
| Sun | 31 Jan 1999 | Batley | 40 | Lock Lane | 10 | | Mount Pleasant | 713 | > |
| Sun | 31 Jan 1999 | Bramley | 12 | Leigh Miners R. | 18 | | Headingley | | > |
| Sun | 31 Jan 1999 | Dewsbury | 38 | Siddal | 10 | | Ram Stadium | 1,427 | > |
| Sun | 31 Jan 1999 | Doncaster | 35 | Oldham St Annes | 24 | | Tattersfield | 1,614 | > |
| Sun | 31 Jan 1999 | Featherstone R. | 70 | Thornhill | 6 | | Lionheart | 1,187 | > |
| Sun | 31 Jan 1999 | Hemel | 8 | Featherstone Lions | 29 | | Pennine Way | 286 | > |
| Sun | 31 Jan 1999 | Hull KR | 56 | Wath Brow Hornets | 4 | | Craven Park | 1,907 | > |
| Sun | 31 Jan 1999 | Hunslet | 66 | Townville | 6 | | John Charles | 749 | > |
| Sun | 31 Jan 1999 | Keighley | 48 | Rochdale Mayfield | 2 | | Cougar | 2,219 | > |
| Sun | 31 Jan 1999 | Lancashire | 50 | Askam | 3 | | Victory Park | 408 | > |
| Sun | 31 Jan 1999 | Leigh | 42 | Norland | 6 | | Coliseum | 1,400 | > |
| Sun | 31 Jan 1999 | Rochdale H. | 52 | Wigan St Judes | 12 | | Spotland | 883 | > |
| Sun | 31 Jan 1999 | Swinton | 38 | Moldgreen | 4 | | Gigg Lane | 915 | > |
| Sun | 31 Jan 1999 | Whitehaven | 22 | Saddleworth | 6 | | Recreation Gnd | 779 | > |
| Sun | 31 Jan 1999 | Widnes | 34 | West Hull | 4 | | AutoQuest | 2,412 | > |
| Sun | 31 Jan 1999 | Workington | 30 | Skirlaugh | 4 | | Derwent Park | 1,316 | > |
| Sun | 31 Jan 1999 | York | 57 | Egremont | 2 | | South Ryedale | 768 | > |
| Mon | 01 Feb 1999 | Oldham | 26 | Eccles | 7 | | Spotland | 883 | > |
| Challenge Cup - Round 4
|
|---|
| Fri | 12 Feb 1999 | Wakefield T. | 12 | Batley | 2 | | Belle Vue | 2,106 | > |
| Sat | 13 Feb 1999 | Featherstone Lions | 6 | Halifax | 74 | | Millpond Stadium | 1,533 | > |
| Sat | 13 Feb 1999 | Leigh Miners R. | 0 | Hull KR | 52 | | Twist Lane | 1,317 | > |
| Sat | 13 Feb 1999 | Salford | 16 | Sheffield | 6 | | The Willows | 2,359 | > |
| Sun | 14 Feb 1999 | Barrow | 16 | Leigh | 33 | | Craven Park | 1,485 | > |
| Sun | 14 Feb 1999 | Bradford | 92 | Workington | 0 | | Odsal | 7,593 | > |
| Sun | 14 Feb 1999 | Castleford | 36 | Hull | 22 | | Wheldon Road | 6,107 | > |
| Sun | 14 Feb 1999 | Huddersfield | 78 | Swinton | 4 | | Alfred McAlpine | 2,277 | > |
| Sun | 14 Feb 1999 | Hunslet | 10 | St Helens | 40 | | John Charles | 2,200 | > |
| Sun | 14 Feb 1999 | Leeds | 28 | Wigan | 18 | | Headingley | 18,000 | > |
| Sun | 14 Feb 1999 | London | 64 | Doncaster | 0 | | The Stoop | 2,164 | > |
| Sun | 14 Feb 1999 | Rochdale H. | 19 | York | 22 | | Spotland | 609 | > |
| Sun | 14 Feb 1999 | Warrington | 50 | Featherstone R. | 6 | S. Nicholson | Wilderspool | 4,335 | > |
| Sun | 14 Feb 1999 | Whitehaven | 24 | Lancashire | 6 | | Recreation Gnd | 827 | > |
| Sun | 14 Feb 1999 | Widnes | 28 | Keighley | 20 | | AutoQuest | 3,003 | > |
| Mon | 15 Feb 1999 | Oldham | 18 | Dewsbury | 10 | | Boundary | 1,620 | > |
| Challenge Cup - Round 5
|
|---|
| Fri | 26 Feb 1999 | Castleford | 28 | York | 2 | N. Oddy | Wheldon Road | 5,411 | > |
| Sat | 27 Feb 1999 | Leeds | 24 | St Helens | 16 | S. Cummings | Headingley | 14,162 | > |
| Sun | 28 Feb 1999 | Huddersfield | 14 | Salford | 22 | S. Presley | Alfred McAlpine | 4,992 | > |
| Sun | 28 Feb 1999 | Hull KR | 0 | London | 6 | J. Connolly | Craven Park | 3,971 | > |
| Sun | 28 Feb 1999 | Wakefield T. | 8 | Bradford | 26 | S. Nicholson | Belle Vue | 7,385 | > |
| Sun | 28 Feb 1999 | Warrington | 34 | Halifax | 4 | R. Smith | Wilderspool | 5,102 | > |
| Sun | 28 Feb 1999 | Whitehaven | 18 | Oldham | 2 | K. Kirkpatrick | Recreation Gnd | 1,438 | > |
| Sun | 28 Feb 1999 | Widnes | 20 | Leigh | 17 | S. Ganson | AutoQuest | 4,054 | > |
| Challenge Cup - Quarter Final
|
|---|
| Sat | 13 Mar 1999 | Castleford | 30 | Salford | 10 | S. Cummings | Wheldon Road | 5,236 | > |
| Sun | 14 Mar 1999 | Bradford | 52 | Warrington | 16 | J. Connolly | Odsal | 10,430 | > |
| Sun | 14 Mar 1999 | London | 54 | Whitehaven | 6 | R. Smith | The Stoop | 1,598 | > |
| Sun | 14 Mar 1999 | Widnes | 10 | Leeds | 46 | S. Presley | AutoQuest | 6,375 | > |
| Challenge Cup - Semi Final
|
|---|
| Sat | 27 Mar 1999 | Castleford | 27 | London | 33 | S. Cummings | Headingley | 7,561 | > |
| Sun | 28 Mar 1999 | Bradford | 10 | Leeds | 23 | R. Smith | Alfred McAlpine | 23,438 | > |
| Challenge Cup - Final
|
|---|
| Sat | 01 May 1999 | Leeds | 52 | London | 16 | R. Smith | Wembley | 73,242 | > |