Aberdare| 5 | | Trinity Street | | > | | Sat | 12 Dec 1908 | Mid Rhondda | 8 | Treherbert | 7 | | Athletic Ground | | > |
| Sat | 26 Dec 1908 | Mid Rhondda | 2 | Barry | 0 | | Athletic Ground | | > |
| Challenge Cup - Round 1
|
|---|
| Sat | 27 Feb 1909 | Barrow St.George's | 0 | Barrow | 36 | | Cavendish Park | | > |
| Sat | 27 Feb 1909 | Beverley | 7 | Ebbw Vale | 2 | | Boulevard | | > |
| Sat | 27 Feb 1909 | Bradford N. | 3 | Wakefield T. | 13 | | Birch Lane | | > |
| Sat | 27 Feb 1909 | Bramley | 13 | Broughton R. | 23 | | Barley Mow | | > |
| Sat | 27 Feb 1909 | Halifax | 15 | St Helens | 8 | | Thrum | | > |
| Sat | 27 Feb 1909 | Hunslet | 25 | Mid Rhondda | 5 | | Parkside | | > |
| Sat | 27 Feb 1909 | Leigh | 6 | Batley | 5 | | Mather Lane | | > |
| Sat | 27 Feb 1909 | Normanton | 10 | Hull | 20 | | Horsfalls | | > |
| Sat | 27 Feb 1909 | Oldham | 8 | Hull KR | 7 | | Watersheddings | | > |
| Sat | 27 Feb 1909 | Pemberton Rovers | 6 | Keighley | 41 | | [unknown] | | > |
| Sat | 27 Feb 1909 | Rochdale H. | 3 | Swinton | 3 | | Athletic Ground | | > |
| Sat | 27 Feb 1909 | Runcorn | 23 | Egremont | 5 | | Canal St | | > |
| Sat | 27 Feb 1909 | Salford | 28 | Dewsbury | 0 | | Weaste | | > |
| Sat | 27 Feb 1909 | Warrington | 3 | Leeds | 5 | | Wilderspool | | > |
| Sat | 27 Feb 1909 | Widnes | 2 | Huddersfield | 25 | | Fartown | | > |
| Sat | 27 Feb 1909 | Wigan | 20 | York | 7 | | Central Park | | > |
| Wed | 03 Mar 1909 | Swinton | 3 | Rochdale H. | 0 | | Chorley Road | | > |
| Challenge Cup - Round 2
|
|---|
| Sat | 13 Mar 1909 | Broughton R. | 0 | Salford | 4 | | Wheater's | | > |
| Sat | 13 Mar 1909 | Halifax | 53 | Beverley | 2 | | Thrum | | > |
| Sat | 13 Mar 1909 | Huddersfield | 34 | Barrow | 3 | | Fartown | | > |
| Sat | 13 Mar 1909 | Hunslet | 15 | Leeds | 9 | | Parkside | | > |
| Sat | 13 Mar 1909 | Leigh | 3 | Wakefield T. | 9 | | Mather Lane | | > |
| Sat | 13 Mar 1909 | Runcorn | 9 | Hull | 11 | | Canal St | | > |
| Sat | 13 Mar 1909 | Swinton | 3 | Oldham | 3 | | Chorley Road | | > |
| Sat | 13 Mar 1909 | Wigan | 47 | Keighley | 0 | | Central Park | | > |
| Tue | 16 Mar 1909 | Oldham | 17 | Swinton | 3 | | Watersheddings | | > |
| Challenge Cup - Round 3
|
|---|
| Sat | 27 Mar 1909 | Huddersfield | 10 | Wigan | 10 | | Fartown | | > |
| Sat | 27 Mar 1909 | Oldham | 6 | Hull | 13 | | Watersheddings | | > |
| Sat | 27 Mar 1909 | Salford | 7 | Halifax | 13 | | Weaste | | > |
| Sat | 27 Mar 1909 | Wakefield T. | 19 | Hunslet | 0 | | Belle Vue | | > |
| Wed | 31 Mar 1909 | Wigan | 16 | Huddersfield | 3 | | Central Park | | > |
| Challenge Cup - Semi Final
|
|---|
| Sat | 10 Apr 1909 | Halifax | 4 | Hull | 10 | | Fartown | 21,800 | > |
| Sat | 10 Apr 1909 | Wigan | 2 | Wakefield T. | 14 | | Wheater's | 18,000 | > |
| Challenge Cup - Final
|
|---|
| Sat | 24 Apr 1909 | Wakefield T. | 17 | Hull | 0 | | Headingley | 23,587 | > |