| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers | Ladies | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Charlton Manager | |
| 1923/24 | FA Cup | 2 February 1924 | The Mount | D | 0-0 | George Jobey | Bill Rayner |
| 1923/24 | FA Cup | 6 February 1924 | Molineux | W | 1-0 | George Jobey | Bill Rayner |
| 1929/30 | Football League (2) | 26 December 1929 | Molineux | L | 0-4 | Major Frank Buckley | Alex McFarlane |
| 1929/30 | Football League (2) | 1 January 1930 | The Valley | L | 0-2 | Major Frank Buckley | Alex McFarlane |
| 1930/31 | Football League (2) | 6 December 1930 | The Valley | W | 2-1 | Major Frank Buckley | Alex McFarlane |
| 1930/31 | Football League (2) | 11 April 1931 | Molineux | D | 1-1 | Major Frank Buckley | Alex McFarlane |
| 1931/32 | Football League (2) | 28 December 1931 | Molineux | W | 3-1 | Major Frank Buckley | Alex McFarlane |
| 1931/32 | Football League (2) | 7 May 1932 | The Valley | L | 2-3 | Major Frank Buckley | Alex McFarlane |
| 1936/37 | Football League (1) | 21 November 1936 | Molineux | W | 6-1 | Major Frank Buckley | Jimmy Seed |
| 1936/37 | Football League (1) | 27 March 1937 | The Valley | L | 0-4 | Major Frank Buckley | Jimmy Seed |
| 1937/38 | Football League (1) | 13 November 1937 | Molineux | D | 1-1 | Major Frank Buckley | Jimmy Seed |
| 1937/38 | Football League (1) | 26 March 1938 | The Valley | L | 1-4 | Major Frank Buckley | Jimmy Seed |
| 1938/39 | Football League (1) | 10 December 1938 | The Valley | W | 4-0 | Major Frank Buckley | Jimmy Seed |
| 1938/39 | Football League (1) | 15 April 1939 | Molineux | W | 3-1 | Major Frank Buckley | Jimmy Seed |
| 1945/46 | War Competition | 27 August 1945 | Molineux | W | 2-1 | Ted Vizard | Jimmy Seed |
| 1945/46 | FA Cup | 26 January 1946 | The Valley | L | 2-5 | Ted Vizard | Jimmy Seed |
| 1945/46 | FA Cup | 30 January 1946 | Molineux | D | 1-1 | Ted Vizard | Jimmy Seed |
| 1945/46 | War Competition | 4 May 1946 | The Valley | D | 1-1 | Ted Vizard | Jimmy Seed |
| 1946/47 | Football League (1) | 9 November 1946 | The Valley | W | 4-1 | Ted Vizard | Jimmy Seed |
| 1946/47 | Football League (1) | 15 March 1947 | Molineux | W | 2-0 | Ted Vizard | Jimmy Seed |
| 1947/48 | Football League (1) | 11 October 1947 | The Valley | L | 1-5 | Ted Vizard | Jimmy Seed |
| 1947/48 | Football League (1) | 28 February 1948 | Molineux | W | 2-0 | Ted Vizard | Jimmy Seed |
| 1948/49 | Football League (1) | 6 November 1948 | Molineux | W | 2-0 | Stan Cullis | Jimmy Seed |
| 1948/49 | Football League (1) | 13 April 1949 | The Valley | W | 3-2 | Stan Cullis | Jimmy Seed |
| 1949/50 | Football League (1) | 24 August 1949 | The Valley | W | 3-2 | Stan Cullis | Jimmy Seed |
| 1949/50 | Football League (1) | 29 August 1949 | Molineux | W | 2-1 | Stan Cullis | Jimmy Seed |
| 1950/51 | Football League (1) | 23 September 1950 | The Valley | L | 2-3 | Stan Cullis | Jimmy Seed |
| 1950/51 | Football League (1) | 3 February 1951 | Molineux | L | 2-3 | Stan Cullis | Jimmy Seed |
| 1951/52 | Football League (1) | 24 November 1951 | Molineux | D | 2-2 | Stan Cullis | Jimmy Seed |
| 1951/52 | Football League (1) | 12 April 1952 | The Valley | L | 0-1 | Stan Cullis | Jimmy Seed |
| 1952/53 | Football League (1) | 30 August 1952 | The Valley | D | 2-2 | Stan Cullis | Jimmy Seed |
| 1952/53 | Football League (1) | 3 January 1953 | Molineux | L | 1-2 | Stan Cullis | Jimmy Seed |
| 1953/54 | Football League (1) | 21 November 1953 | The Valley | W | 2-0 | Stan Cullis | Jimmy Seed |
| 1953/54 | Football League (1) | 10 April 1954 | Molineux | W | 5-0 | Stan Cullis | Jimmy Seed |
| 1954/55 | Football League (1) | 11 September 1954 | The Valley | W | 3-1 | Stan Cullis | Jimmy Seed |
| 1954/55 | Football League (1) | 22 January 1955 | Molineux | W | 2-1 | Stan Cullis | Jimmy Seed |
| 1954/55 | FA Cup | 19 February 1955 | Molineux | W | 4-1 | Stan Cullis | Jimmy Seed |
| 1955/56 | Football League (1) | 12 November 1955 | Molineux | W | 2-0 | Stan Cullis | Jimmy Seed |
| 1955/56 | Football League (1) | 24 March 1956 | The Valley | W | 2-0 | Stan Cullis | Jimmy Seed |
| 1956/57 | Football League (1) | 25 December 1956 | The Valley | L | 1-2 | Stan Cullis | Jimmy Trotter |
| 1956/57 | Football League (1) | 16 February 1957 | Molineux | W | 7-3 | Stan Cullis | Jimmy Trotter |
| 1959/60 | FA Cup | 30 January 1960 | Molineux | W | 2-1 | Stan Cullis | Jimmy Trotter |
| 1964/65 | Friendly | 17 August 1964 | The Valley | L | 1-3 | Stan Cullis | Frank Hill |
| 1965/66 | Football League (2) | 13 November 1965 | Molineux | D | 2-2 | Andy Beattie © | Bob Stokoe |
| 1965/66 | Football League (2) | 8 January 1966 | The Valley | D | 1-1 | Andy Beattie © | Bob Stokoe |
| 1966/67 | Football League (2) | 1 October 1966 | Molineux | W | 1-0 | Ronnie Allen | Bob Stokoe |
| 1966/67 | Football League (2) | 11 February 1967 | The Valley | W | 3-1 | Ronnie Allen | Bob Stokoe |
| 1975/76 | FA Cup | 14 February 1976 | Molineux | W | 3-0 | Bill McGarry | Andy Nelson |
| 1976/77 | Football League (2) | 4 September 1976 | Molineux | W | 3-0 | Sammy Chung | Andy Nelson |
| 1976/77 | Football League (2) | 12 February 1977 | The Valley | D | 1-1 | Sammy Chung | Andy Nelson |
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