| Round | Date | Opponent | Result | Scorers |
|---|---|---|---|---|
| R1 | 13/10/1888 | Heeley Olympic | 3 – 3 | Carr 1.2og, Whyke 1.3, Berry 2.6 <br> (Xxx 1.1og, Sharman H 1.4, Sharman J 2.5) |
| R1R | 27/10/1888 | Heeley Olympic | 3 – 1 | Whyke 1G, Taylor R 2G, Taylor G 4G <br> (Xxx 3G2H) |
| R2 | 3/11/1888 | Staveley | 0 – 12 | Willis 5, Marshall 2G, 3G, 8G, 9G, 12G, Wilshaw 4G, Cropper 5G, 6G2H, 7G, 11G, Potter 10G |
- 15/9/1888 A Sheffield Ellesmore 4 – 1 Whyke, Midgley
- 29/9/1888 A Park Grange 3 – 2 R Taylor, Whyke 2
- 6/10/1888 H Mexborough 4 – 2 600 R Taylor 2, Walker 2 (Law 2.5, Lovatt 2.6)
- 20/10/1888 H Tankersley United 8 – 0
- 10/11/1888 H Wombwell Town 5 – 0 G Taylor 2, Midgley 2, Hirst
- 17/11/1888 H Ardsley Woodman Rangers 3 – 2 R Taylor, G Taylor, Whyke
- 24/11/1888 H Carlton 3 – 0
- 24/11/1888 A Worsborough Dale 4 – 2
- 1/12/1888 A Doncaster Rovers 0 – 6
- 8/12/1888 A Mexborough 0 – 2
- 15/12/1888 H Sheffield Ellesmore 3 – 0
- 26/12/1888 H Bulwell (Notts) 0 – 0
- 29/12/1888 H Staincross 4 – 2
- 1/1/1889 H Sheffield Clinton 1 – 4
- 12/1/1889 A Leeds Association 1 – 3 Cooper OG
- 19/1/1889 A Thurlstone 2 – 1
- 26/1/1889 A Springfield Star 3 – 3
- 26/1/1889 H Worsborough Dale 3 – 1
- 2/2/1889 A Wombwell Town 1 – 1
- 9/2/1889 A Spring Victoria 2 – 3
- 23/2/1889 H Park Grange 2 – 1 Nixon, Raley
- 2/3/1889 H Sheffield Club 4 – 2 Raley
- 23/3/1889 H Thurlstone 3 – 5
- 30/3/1889 H Leeds Association 2 – 1
- 6/4/1889 A Staincross 7 – 3
- 13/4/1889 H Barnsley and District 4 – 0
- 22/4/1889 H Ardsley Old 1 – 3