| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers |
| Season | Competition | Date | Venue | Results | |
| 1908/09 | Football League | 1 September 1908 | White Hart Lane | L | 0-3 |
| 1908/09 | Football League | 28 December 1908 | Molineux | W | 1-0 |
| 1919/20 | Football League | 2 April 1920 | White Hart Lane | L | 2-4 |
| 1919/20 | Football League | 5 April 1920 | Molineux | L | 1-3 |
| 1920/21 | FA Cup | 23 April 1921 | Stamford Bridge | L | 0-1 |
| 1928/29 | Football League | 8 September 1928 | White Hart Lane | L | 2-3 |
| 1928/29 | Football League | 19 January 1929 | Molineux | W | 4-2 |
| 1929/30 | Football League | 19 October 1929 | Molineux | W | 3-0 |
| 1929/30 | Football League | 22 February 1930 | White Hart Lane | L | 2-4 |
| 1930/31 | Football League | 6 September 1930 | Molineux | W | 3-1 |
| 1930/31 | Football League | 3 January 1931 | White Hart Lane | L | 0-1 |
| 1931/32 | Football League | 29 August 1931 | Molineux | W | 4-0 |
| 1931/32 | Football League | 2 January 1932 | White Hart Lane | D | 3-3 |
| 1933/34 | Football League | 28 August 1933 | White Hart Lane | L | 0-4 |
| 1933/34 | Football League | 4 September 1933 | Molineux | W | 1-0 |
| 1934/35 | Football League | 8 September 1934 | White Hart Lane | L | 1-3 |
| 1934/35 | Football League | 19 January 1935 | Molineux | W | 6-2 |
| 1945/46 | War Competition | 25 August 1945 | White Hart Lane | W | 4-1 |
| 1945/46 | War Competition | 1 September 1945 | Molineux | W | 4-2 |
| 1950/51 | Football League | 16 September 1950 | Molineux | W | 2-1 |
| 1950/51 | Football League | 20 January 1951 | White Hart Lane | L | 1-2 |
| 1951/52 | Football League | 3 November 1951 | White Hart Lane | L | 2-4 |
| 1951/52 | Football League | 22 March 1952 | Molineux | D | 1-1 |
| 1952/53 | Football League | 6 December 1952 | Molineux | D | 0-0 |
| 1952/53 | Football League | 25 April 1953 | White Hart Lane | L | 2-3 |
| 1953/54 | Football League | 5 December 1953 | White Hart Lane | W | 3-2 |
| 1953/54 | Football League | 24 April 1954 | Molineux | W | 2-0 |
| 1954/55 | Football League | 25 August 1954 | White Hart Lane | L | 2-3 |
| 1954/55 | Football League | 30 August 1954 | Molineux | W | 4-2 |
| 1955/56 | Football League | 19 November 1955 | White Hart Lane | L | 1-2 |
| 1955/56 | Football League | 18 April 1956 | Molineux | W | 5-1 |
| 1956/57 | Football League | 8 September 1956 | White Hart Lane | L | 1-4 |
| 1956/57 | Football League | 12 January 1957 | Molineux | W | 3-0 |
| 1957/58 | Football League | 2 October 1957 | Molineux | W | 4-0 |
| 1957/58 | Football League | 26 December 1957 | White Hart Lane | L | 0-1 |
| 1958/59 | Football League | 27 September 1958 | White Hart Lane | L | 1-2 |
| 1958/59 | Football League | 2 March 1959 | Molineux | D | 1-1 |
| 1959/60 | Football League | 10 October 1959 | White Hart Lane | L | 1-5 |
| 1959/60 | Football League | 23 April 1960 | Molineux | L | 1-3 |
| 1960/61 | Football League | 1 October 1960 | Molineux | L | 0-4 |
| 1960/61 | Football League | 22 February 1961 | White Hart Lane | D | 1-1 |
| 1961/62 | Football League | 16 September 1961 | White Hart Lane | L | 0-1 |
| 1961/62 | Football League | 3 February 1962 | Molineux | W | 3-1 |
| 1962/63 | Football League | 12 September 1962 | White Hart Lane | W | 2-1 |
| 1962/63 | Football League | 19 September 1962 | Molineux | D | 2-2 |
| 1963/64 | Football League | 28 August 1963 | Molineux | L | 1-4 |
| 1963/64 | Football League | 4 September 1963 | White Hart Lane | L | 3-4 |
| 1964/65 | Football League | 14 November 1964 | Molineux | W | 3-1 |
| 1964/65 | Football League | 27 March 1965 | White Hart Lane | L | 4-7 |
| 1967/68 | Football League | 6 September 1967 | White Hart Lane | L | 1-2 |
| 1967/68 | Football League | 11 May 1968 | Molineux | W | 2-1 |
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