Brookhouse| 5 | | Naughton | | > | | Sat | 26 Feb 1966 | Barrow | 11 | Crosfields | 2 | | Craven Park | | > |
| Sat | 26 Feb 1966 | Batley | 4 | Huddersfield | 4 | | Mount Pleasant | | > |
| Sat | 26 Feb 1966 | Blackpool B. | 2 | Workington | 16 | | Borough Park | | > |
| Sat | 26 Feb 1966 | Bradford N. | 23 | Doncaster | 2 | | Odsal | | > |
| Sat | 26 Feb 1966 | Bramley | 5 | Hull KR | 5 | | Headingley | | > |
| Sat | 26 Feb 1966 | Featherstone R. | 22 | Rochdale H. | 6 | | Post Office Road | | > |
| Sat | 26 Feb 1966 | Hull | 11 | Salford | 2 | | Boulevard | | > |
| Sat | 26 Feb 1966 | Hunslet | 7 | Whitehaven | 9 | | Parkside | | > |
| Sat | 26 Feb 1966 | Keighley | 4 | Dewsbury | 5 | | Lawkholme Lane | | > |
| Sat | 26 Feb 1966 | Leeds | 17 | York | 4 | | Headingley | | > |
| Sat | 26 Feb 1966 | Leigh | 15 | Liverpool C. | 6 | | Hilton Park | | > |
| Sat | 26 Feb 1966 | Swinton | 18 | Whitehaven | 5 | | Station Road | | > |
| Sat | 26 Feb 1966 | Wakefield T. | 0 | St Helens | 10 | | Belle Vue | | > |
| Sat | 26 Feb 1966 | Warrington | 15 | Castleford | 7 | | Wilderspool | | > |
| Sat | 26 Feb 1966 | Wigan | 8 | Halifax | 4 | | Central Park | | > |
| Tue | 01 Mar 1966 | Huddersfield | 23 | Batley | 5 | | Fartown | | > |
| Tue | 01 Mar 1966 | Hull KR | 7 | Bramley | 2 | | Craven Park | | > |
| Challenge Cup - Round 2
|
|---|
| Sat | 19 Mar 1966 | Dewsbury | 23 | Barrow | 15 | | Crown Flatt | | > |
| Sat | 19 Mar 1966 | Featherstone R. | 14 | Warrington | 15 | | Post Office Road | | > |
| Sat | 19 Mar 1966 | Huddersfield | 8 | Leigh | 0 | | Fartown | | > |
| Sat | 19 Mar 1966 | Leeds | 22 | Hull | 12 | | Headingley | | > |
| Sat | 19 Mar 1966 | St Helens | 16 | Swinton | 4 | | Knowsley | | > |
| Sat | 19 Mar 1966 | Widnes | 6 | Bradford N. | 7 | | Naughton | | > |
| Sat | 19 Mar 1966 | Wigan | 40 | Whitehaven | 6 | | Central Park | | > |
| Sat | 19 Mar 1966 | Workington | 5 | Hull KR | 7 | | Derwent Park | | > |
| Challenge Cup - Round 3
|
|---|
| Mon | 04 Apr 1966 | St Helens | 12 | Hull KR | 10 | | Knowsley | | > |
| Tue | 05 Apr 1966 | Dewsbury | 8 | Huddersfield | 2 | | Crown Flatt | | > |
| Wed | 06 Apr 1966 | Bradford N. | 6 | Wigan | 15 | | Odsal | | > |
| Wed | 06 Apr 1966 | Warrington | 2 | Leeds | 2 | | Wilderspool | | > |
| Fri | 15 Apr 1966 | Leeds | 8 | Warrington | 0 | | Headingley | | > |
| Challenge Cup - Semi Final
|
|---|
| Sat | 16 Apr 1966 | St Helens | 12 | Dewsbury | 5 | | Station Road | 13,046 | > |
| Sat | 23 Apr 1966 | Leeds | 2 | Wigan | 7 | | Fartown | 22,758 | > |
| Challenge Cup - Final
|
|---|
| Sat | 21 May 1966 | St Helens | 21 | Wigan | 2 | | Wembley | 98,536 | > |