| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Chelsea Manager | |
| 1906/07 | Football League (2) | 8 December 1906 | Molineux | L | 1-2 | Jack Addenbrooke | John Tait Robertson |
| 1906/07 | Football League (2) | 13 April 1907 | Stamford Bridge | L | 0-4 | Jack Addenbrooke | John Tait Robertson |
| 1910/11 | Football League (2) | 24 September 1910 | Stamford Bridge | L | 0-2 | Jack Addenbrooke | David Calderhead ‘jnr’ |
| 1910/11 | Football League (2) | 28 January 1911 | Molineux | D | 0-0 | Jack Addenbrooke | David Calderhead ‘jnr’ |
| 1910/11 | FA Cup | 25 February 1911 | Molineux | L | 0-2 | Jack Addenbrooke | David Calderhead ‘jnr’ |
| 1911/12 | Football League (2) | 16 September 1911 | Stamford Bridge | L | 0-4 | Jack Addenbrooke | David Calderhead ‘jnr’ |
| 1911/12 | Football League (2) | 20 January 1912 | Molineux | W | 3-1 | Jack Addenbrooke | David Calderhead ‘jnr’ |
| 1924/25 | Football League (2) | 25 December 1924 | Stamford Bridge | L | 0-1 | Albert Hoskins | David Calderhead ‘jnr’ |
| 1924/25 | Football League (2) | 26 December 1924 | Molineux | L | 0-1 | Albert Hoskins | David Calderhead ‘jnr’ |
| 1925/26 | Football League (2) | 14 November 1925 | Molineux | D | 0-0 | Albert Hoskins | David Calderhead ‘jnr’ |
| 1925/26 | Football League (2) | 27 March 1926 | Stamford Bridge | D | 3-3 | Fred Scotchbrook | David Calderhead ‘jnr’ |
| 1926/27 | Football League (2) | 30 August 1926 | Molineux | L | 0-3 | Fred Scotchbrook | David Calderhead ‘jnr’ |
| 1926/27 | Football League (2) | 18 April 1927 | Stamford Bridge | L | 0-1 | Fred Scotchbrook | David Calderhead ‘jnr’ |
| 1927/28 | Football League (2) | 17 December 1927 | Stamford Bridge | L | 0-2 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1927/28 | FA Cup | 14 January 1928 | Molineux | W | 2-1 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1927/28 | Football League (2) | 28 April 1928 | Molineux | L | 1-2 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1928/29 | Football League (2) | 3 November 1928 | Molineux | D | 1-1 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1928/29 | Football League (2) | 16 March 1929 | Stamford Bridge | W | 2-0 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1929/30 | Football League (2) | 23 November 1929 | Stamford Bridge | D | 1-1 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1929/30 | Football League (2) | 29 March 1930 | Molineux | L | 0-1 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1932/33 | Football League (1) | 17 September 1932 | Molineux | L | 1-2 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1932/33 | Football League (1) | 28 January 1933 | Stamford Bridge | L | 1-3 | Major Frank Buckley | David Calderhead ‘jnr’ |
| 1933/34 | Football League (1) | 2 September 1933 | Stamford Bridge | L | 2-5 | Major Frank Buckley | Leslie Knighton |
| 1933/34 | Football League (1) | 6 January 1934 | Molineux | D | 1-1 | Major Frank Buckley | Leslie Knighton |
| 1934/35 | Football League (1) | 19 April 1935 | Stamford Bridge | L | 2-4 | Major Frank Buckley | Leslie Knighton |
| 1934/35 | Football League (1) | 22 April 1935 | Molineux | W | 6-1 | Major Frank Buckley | Leslie Knighton |
| 1935/36 | Football League (1) | 21 December 1935 | Stamford Bridge | D | 2-2 | Major Frank Buckley | Leslie Knighton |
| 1935/36 | Football League (1) | 25 April 1936 | Molineux | D | 3-3 | Major Frank Buckley | Leslie Knighton |
| 1936/37 | Football League (1) | 7 November 1936 | Molineux | L | 1-2 | Major Frank Buckley | Leslie Knighton |
| 1936/37 | Football League (1) | 13 March 1937 | Stamford Bridge | L | 1-0 | Major Frank Buckley | Leslie Knighton |
| 1937/38 | Football League (1) | 18 December 1937 | Stamford Bridge | W | 2-0 | Major Frank Buckley | Leslie Knighton |
| 1937/38 | Football League (1) | 30 April 1938 | Molineux | D | 1-1 | Major Frank Buckley | Leslie Knighton |
| 1938/39 | Football League (1) | 26 November 1938 | Stamford Bridge | W | 3-1 | Major Frank Buckley | Leslie Knighton |
| 1938/39 | Football League (1) | 1 April 1939 | Molineux | W | 2-0 | Major Frank Buckley | Leslie Knighton |
| 1946/47 | Football League (1) | 21 December 1946 | Stamford Bridge | W | 2-1 | Ted Vizard | Billy Birrell |
| 1946/47 | Football League (1) | 26 April 1947 | Molineux | W | 6-4 | Ted Vizard | Billy Birrell |
| 1947/48 | Football League (1) | 27 September 1947 | Molineux | W | 1-0 | Ted Vizard | Billy Birrell |
| 1947/48 | Football League (1) | 14 February 1948 | Stamford Bridge | D | 1-1 | Ted Vizard | Billy Birrell |
| 1948/49 | Football League (1) | 11 December 1948 | Stamford Bridge | L | 1-4 | Stan Cullis | Billy Birrell |
| 1948/49 | Football League (1) | 7 May 1949 | Molineux | D | 1-1 | Stan Cullis | Billy Birrell |
| 1949/50 | Football League (1) | 29 October 1949 | Molineux | D | 2-2 | Stan Cullis | Billy Birrell |
| 1949/50 | Football League (1) | 15 April 1950 | Stamford Bridge | D | 0-0 | Stan Cullis | Billy Birrell |
| 1950/51 | Football League (1) | 21 October 1950 | Molineux | W | 2-1 | Stan Cullis | Billy Birrell |
| 1950/51 | Football League (1) | 25 April 1951 | Stamford Bridge | L | 1-2 | Stan Cullis | Billy Birrell |
| 1951/52 | Football League (1) | 22 September 1951 | Molineux | W | 5-3 | Stan Cullis | Billy Birrell |
| 1951/52 | Football League (1) | 26 January 1952 | Stamford Bridge | L | 1-0 | Stan Cullis | Billy Birrell |
| 1952/53 | Football League (1) | 27 September 1952 | Stamford Bridge | W | 2-1 | Stan Cullis | Ted Drake |
| 1952/53 | Football League (1) | 18 February 1953 | Molineux | D | 2-2 | Stan Cullis | Ted Drake |
| 1953/54 | Football League (1) | 26 September 1953 | Molineux | W | 8-1 | Stan Cullis | Ted Drake |
| 1953/54 | Football League (1) | 13 February 1954 | Stamford Bridge | L | 2-4 | Stan Cullis | Ted Drake |
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