Leigh Miners W.| 0 | | Central Park | | > | | Sat | 25 Jan 1969 | Dewsbury | 7 | Bradford N. | 21 | | Crown Flatt | | > |
| Sat | 25 Jan 1969 | Halifax | 12 | Leeds | 17 | | Thrum | | > |
| Sat | 25 Jan 1969 | Hull | 3 | St Helens | 13 | | Boulevard | | > |
| Sat | 25 Jan 1969 | Hunslet | 7 | Castleford | 19 | | Parkside | | > |
| Sat | 25 Jan 1969 | Keighley | 23 | Whitehaven | 2 | | Lawkholme Lane | | > |
| Sat | 25 Jan 1969 | Leigh | 4 | Rochdale H. | 13 | | Hilton Park | | > |
| Sat | 25 Jan 1969 | Oldham | 12 | Hull KR | 10 | | Watersheddings | | > |
| Sat | 25 Jan 1969 | Salford | 17 | Batley | 2 | | The Willows | | > |
| Sat | 25 Jan 1969 | Wakefield T. | 50 | Ackworth | 7 | | Belle Vue | | > |
| Sat | 25 Jan 1969 | Workington | 5 | Swinton | 2 | | Derwent Park | | > |
| Sun | 26 Jan 1969 | Doncaster | 3 | Featherstone R. | 4 | | Tattersfield | | > |
| Sun | 26 Jan 1969 | Huddersfield | 13 | Barrow | 5 | | Fartown | | > |
| Sun | 26 Jan 1969 | Widnes | 23 | York | 8 | | Naughton | | > |
| Tue | 28 Jan 1969 | Huyton | 2 | Warrington | 5 | | Wilderspool | | > |
| Sat | 01 Feb 1969 | Blackpool B. | 10 | Bramley | 17 | | Borough Park | | > |
| Challenge Cup - Round 2
|
|---|
| Sat | 15 Feb 1969 | Castleford | 12 | Wigan | 8 | | Wheldon Road | | > |
| Sat | 22 Feb 1969 | Warrington | 19 | Huddersfield | 8 | | Wilderspool | | > |
| Sun | 23 Feb 1969 | Rochdale H. | 7 | Bramley | 7 | | Athletic Ground | | > |
| Sun | 23 Feb 1969 | Salford | 12 | Workington | 5 | | The Willows | | > |
| Mon | 24 Feb 1969 | Keighley | 2 | Leeds | 17 | | Lawkholme Lane | | > |
| Tue | 25 Feb 1969 | Oldham | 6 | St Helens | 15 | | Watersheddings | | > |
| Wed | 26 Feb 1969 | Bradford N. | 7 | Wakefield T. | 7 | | Headingley | | > |
| Wed | 26 Feb 1969 | Bramley | 4 | Rochdale H. | 7 | | McLaren | | > |
| Wed | 26 Feb 1969 | Featherstone R. | 7 | Widnes | 9 | | Post Office Road | | > |
| Thu | 27 Feb 1969 | Wakefield T. | 10 | Bradford N. | 0 | | Belle Vue | | > |
| Challenge Cup - Round 3
|
|---|
| Sat | 01 Mar 1969 | Castleford | 9 | Leeds | 5 | | Wheldon Road | | > |
| Sat | 01 Mar 1969 | Wakefield T. | 10 | Rochdale H. | 10 | | Belle Vue | | > |
| Sat | 01 Mar 1969 | Warrington | 4 | St Helens | 2 | | Wilderspool | | > |
| Sun | 02 Mar 1969 | Salford | 20 | Widnes | 7 | | The Willows | | > |
| Wed | 05 Mar 1969 | Rochdale H. | 2 | Wakefield T. | 15 | | Athletic Ground | | > |
| Challenge Cup - Semi Final
|
|---|
| Sat | 22 Mar 1969 | Warrington | 8 | Salford | 15 | | Central Park | 20,600 | > |
| Sat | 29 Mar 1969 | Castleford | 16 | Wakefield T. | 10 | | Headingley | 21,497 | > |
| Challenge Cup - Final
|
|---|
| Sat | 17 May 1969 | Castleford | 11 | Salford | 6 | | Wembley | 97,939 | > |