| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers |
| Season | Competition | Date | Venue | Results | |
| 1968/69 | Football League | 7 December 1968 | Molineux | W | 2-0 |
| 1968/69 | FA Cup | 25 January 1969 | White Hart Lane | L | 1-2 |
| 1968/69 | Football League | 22 February 1969 | White Hart Lane | D | 1-1 |
| 1969/70 | FL Cup | 3 September 1969 | Molineux | W | 1-0 |
| 1969/70 | Football League | 11 October 1969 | White Hart Lane | W | 1-0 |
| 1969/70 | Football League | 7 February 1970 | Molineux | D | 2-2 |
| 1970/71 | Football League | 22 August 1970 | Molineux | L | 0-3 |
| 1970/71 | Football League | 19 December 1970 | White Hart Lane | D | 0-0 |
| 1971/72 | Football League | 14 August 1971 | Molineux | D | 2-2 |
| 1971/72 | Football League | 16 October 1971 | White Hart Lane | L | 1-4 |
| 1971/72 | UEFA Cup | 3 May 1972 | Molineux | L | 1-2 |
| 1971/72 | UEFA Cup | 17 May 1972 | White Hart Lane | D | 1-1 |
| 1972/73 | Football League | 19 August 1972 | Molineux | W | 3-2 |
| 1972/73 | FL Cup | 20 December 1972 | Molineux | L | 1-2 |
| 1972/73 | FL Cup | 30 December 1972 | White Hart Lane | D | 2-2 |
| 1972/73 | Football League | 30 April 1973 | White Hart Lane | D | 2-2 |
| 1973/74 | Football League | 24 November 1973 | White Hart Lane | W | 3-1 |
| 1973/74 | Football League | 6 April 1974 | Molineux | D | 1-1 |
| 1974/75 | Football League | 21 September 1974 | Molineux | L | 2-3 |
| 1974/75 | Football League | 28 March 1975 | White Hart Lane | L | 0-3 |
| 1975/76 | Football League | 1 November 1975 | White Hart Lane | L | 1-2 |
| 1975/76 | Football League | 16 March 1976 | Molineux | L | 0-1 |
| 1978/79 | Friendly | 16 October 1978 | Home | W | 2-1 |
| 1978/79 | Football League | 25 November 1978 | White Hart Lane | L | 0-1 |
| 1978/79 | Football League | 3 April 1979 | Molineux | W | 3-2 |
| 1979/80 | Football League | 5 April 1980 | Molineux | L | 1-2 |
| 1979/90 | Football League | 23 April 1980 | White Hart Lane | D | 2-2 |
| 1980/81 | Football League | 8 November 1980 | White Hart Lane | D | 2-2 |
| 1980/81 | FA Cup | 11 April 1981 | Hillsborough | D | 2-2 |
| 1980/81 | FA Cup | 15 April 1981 | Highbury | L | 0-3 |
| 1980/81 | Football League | 30 April 1981 | Molineux | W | 1-0 |
| 1981/82 | Football League | 12 September 1981 | Molineux | L | 0-1 |
| 1981/82 | Football League | 6 February 1982 | White Hart Lane | L | 1-6 |
| 1983/84 | Football League | 15 October 1983 | Molineux | L | 2-3 |
| 1983/84 | Football League | 31 March 1984 | White Hart Lane | L | 0-1 |
| 1995/96 | FA Cup | 27 January 1996 | White Hart Lane | D | 1-1 |
| 1995/96 | FA Cup | 7 February 1996 | Molineux | L | 0-2 |
| 1999/00 | Friendly | 31 July 1999 | Home | D | 1-1 |
| 2003/04 | Premier League | 6 December 2003 | White Hart Lane | L | 2-5 |
| 2003/04 | Premier League | 15 May 2004 | Molineux | L | 0-2 |
| 2009/10 | Premier League | 12 December 2009 | White Hart Lane | W | 1-0 |
| 2009/10 | Premier League | 10 February 2010 | Molineux | W | 1-0 |
| 2010/11 | Premier League | 18 September 2010 | White Hart Lane | L | 1-3 |
| 2010/11 | Premier League | 6 March 2011 | Molineux | D | 3-3 |
| 2011/12 | Premier League | 10 September 2011 | Molineux | L | 0-2 |
| 2011/12 | Premier League | 14 January 2012 | White Hart Lane | D | 1-1 |
| 2018/19 | Premier League | 3 November 2018 | Molineux | L | 2-3 |
| 2018/19 | Premier League | 29 December 2018 | Wembley Stadium | W | 3-1 |
| 2019/20 | Premier League | 15 December 2019 | Molineux | L | 1-2 |
| 2019/20 | Premier League | 1 March 2020 | Tottenham Hotspur Stadium | W | 3-2 |
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