| First Team Matches | Second Team Matches | Youth Team Matches | League debuts | Associated with both clubs | Transfers | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Barnsley Manager | |
| 1906/07 | Football League (2) | 1 December 1906 | Oakwell Ground | W | 1-0 | Jack Addenbrooke | Arthur Fairclough |
| 1906/07 | Football League (2) | 6 April 1907 | Molineux | W | 5-1 | Jack Addenbrooke | Arthur Fairclough |
| 1907/08 | Football League (2) | 16 November 1907 | Oakwell Ground | L | 0-5 | Jack Addenbrooke | Arthur Fairclough |
| 1907/08 | Football League (2) | 14 March 1908 | Molineux | L | 0-1 | Jack Addenbrooke | Arthur Fairclough |
| 1908/09 | Football League (2) | 19 December 1908 | Molineux | W | 2-0 | Jack Addenbrooke | Arthur Fairclough |
| 1908/09 | Football League (2) | 24 April 1909 | Oakwell Ground | D | 1-1 | Jack Addenbrooke | Arthur Fairclough |
| 1909/10 | Football League (2) | 30 October 1909 | Oakwell Ground | L | 1-7 | Jack Addenbrooke | Arthur Fairclough |
| 1909/10 | Football League (2) | 12 March 1910 | Molineux | W | 1-0 | Jack Addenbrooke | Arthur Fairclough |
| 1910/11 | Football League (2) | 3 September 1910 | Oakwell Ground | D | 2-2 | Jack Addenbrooke | Arthur Fairclough |
| 1910/11 | Football League (2) | 31 December 1910 | Molineux | W | 1-0 | Jack Addenbrooke | Arthur Fairclough |
| 1911/12 | Football League (2) | 11 November 1911 | Oakwell Ground | L | 1-2 | Jack Addenbrooke | Arthur Fairclough |
| 1911/12 | Football League (2) | 16 March 1912 | Molineux | W | 5-0 | Jack Addenbrooke | Arthur Fairclough |
| 1912/13 | Football League (2) | 26 October 1912 | Oakwell Ground | L | 2-3 | Jack Addenbrooke | John Hastie |
| 1912/13 | Football League (2) | 1 March 1913 | Molineux | W | 3-0 | Jack Addenbrooke | John Hastie |
| 1913/14 | Football League (2) | 13 December 1913 | Molineux | L | 0-1 | Jack Addenbrooke | John Hastie |
| 1913/14 | Football League (2) | 18 April 1914 | Oakwell Ground | L | 1-2 | Jack Addenbrooke | Percy Lewis |
| 1914/15 | Football League (2) | 21 November 1914 | Oakwell Ground | L | 1-2 | Jack Addenbrooke | Percy Lewis |
| 1914/15 | Football League (2) | 27 March 1915 | Molineux | W | 4-1 | Jack Addenbrooke | Percy Lewis |
| 1919/20 | Football League (2) | 22 November 1919 | Oakwell Ground | L | 1-4 | Jack Addenbrooke | Peter Sant |
| 1919/20 | Football League (2) | 29 November 1911 | Molineux | L | 2-4 | Jack Addenbrooke | Peter Sant |
| 1920/21 | Football League (2) | 9 October 1920 | Molineux | D | 1-1 | Jack Addenbrooke | Peter Sant |
| 1920/21 | Football League (2) | 16 October 1920 | Oakwell Ground | L | 2-3 | Jack Addenbrooke | Peter Sant |
| 1921/22 | Football League (2) | 10 September 1921 | Oakwell Ground | L | 1-2 | Jack Addenbrooke | Peter Sant |
| 1921/22 | Football League (2) | 17 September 1921 | Molineux | W | 2-0 | Jack Addenbrooke | Peter Sant |
| 1922/23 | Football League (2) | 17 March 1923 | Oakwell Ground | L | 0-1 | George Jobey | Peter Sant |
| 1922/23 | Football League (2) | 24 March 1923 | Molineux | D | 3-3 | George Jobey | Peter Sant |
| 1924/25 | Football League (2) | 1 September 1924 | Oakwell Ground | D | 0-0 | Albert Hoskins | Peter Sant |
| 1924/25 | Football League (2) | 27 April 1925 | Molineux | L | 0-1 | Albert Hoskins | Peter Sant |
| 1925/26 | Football League (2) | 6 March 1926 | Oakwell Ground | D | 1-1 | Albert Hoskins | Peter Sant |
| 1925/26 | Football League (2) | 26 April 1926 | Molineux | W | 7-1 | Fred Scotchbrook | Peter Sant |
| 1926/27 | Football League (2) | 5 November 1926 | Molineux | W | 9-1 | Fred Scotchbrook | John Commins |
| 1926/27 | Football League (2) | 26 March 1927 | Oakwell Ground | L | 1-4 | Fred Scotchbrook | John Commins |
| 1927/28 | Football League (2) | 1 October 1927 | Oakwell Ground | D | 2-2 | Major Frank Buckley | John Commins |
| 1927/28 | Football League (2) | 11 February 1928 | Molineux | W | 2-1 | Major Frank Buckley | John Commins |
| 1928/29 | Football League (2) | 27 October 1928 | Oakwell Ground | D | 2-2 | Major Frank Buckley | Arthur Fairclough |
| 1928/29 | Football League (2) | 9 March 1929 | Molineux | W | 3-1 | Major Frank Buckley | Arthur Fairclough |
| 1929/30 | Football League (2) | 14 December 1929 | Molineux | W | 3-0 | Major Frank Buckley | Arthur Fairclough |
| 1929/30 | Football League (2) | 19 April 1930 | Oakwell Ground | L | 1-3 | Major Frank Buckley | Arthur Fairclough |
| 1930/31 | Football League (2) | 15 November 1930 | Molineux | W | 2-0 | Major Frank Buckley | Brough Fletcher |
| 1930/31 | FA Cup | 14 February 1931 | Oakwell Ground | W | 3-1 | Major Frank Buckley | Brough Fletcher |
| 1930/31 | Football League (2) | 21 March 1931 | Oakwell Ground | L | 0-3 | Major Frank Buckley | Brough Fletcher |
| 1931/32 | Football League (2) | 31 October 1931 | Oakwell Ground | D | 2-2 | Major Frank Buckley | Brough Fletcher |
| 1931/32 | Football League (2) | 12 March 1932 | Molineux | W | 2-0 | Major Frank Buckley | Brough Fletcher |
| 1978/79 | Friendly | 1978 | Away | W | 1-0 | John Barnwell | |
| 1982/83 | Football League (2) | 11 September 1982 | Molineux | W | 2-0 | Graham Hawkins | Norman Hunter |
| 1982/83 | Football League (2) | 5 February 1983 | Oakwell Ground | L | 1-2 | Graham Hawkins | Norman Hunter |
| 1984/85 | Football League (2) | 29 September 1984 | Oakwell Ground | L | 1-5 | Tommy Docherty | Bobby Collins |
| 1984/85 | Football League (2) | 2 February 1985 | Molineux | L | 0-1 | Tommy Docherty | Bobby Collins |
| 1989/90 | Football League (2) | 26 September 1989 | Oakwell Ground | D | 2-2 | Graham Turner | Allan Clarke |
| 1989/90 | Football League (2) | 10 March 1990 | Molineux | D | 1-1 | Graham Turner | Mel Machin |
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