| 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 | |
| 1954/55 | Football League (1) | 4 December 1954 | Molineux | L | 3-4 | Stan Cullis | Ted Drake |
| 1954/55 | Football League (1) | 9 April 1955 | Stamford Bridge | L | 0-1 | Stan Cullis | Ted Drake |
| 1955/56 | Football League (1) | 24 September 1955 | Molineux | W | 2-1 | Stan Cullis | Ted Drake |
| 1955/56 | Football League (1) | 4 February 1956 | Stamford Bridge | W | 3-2 | Stan Cullis | Ted Drake |
| 1956/57 | Football League (1) | 20 October 1956 | Stamford Bridge | D | 3-3 | Stan Cullis | Ted Drake |
| 1956/57 | Football League (1) | 2 March 1957 | Molineux | W | 3-1 | Stan Cullis | Ted Drake |
| 1957/58 | Football League (1) | 19 October 1957 | Molineux | W | 2-1 | Stan Cullis | Ted Drake |
| 1957/58 | Football League (1) | 11 March 1958 | Stamford Bridge | W | 2-1 | Stan Cullis | Ted Drake |
| 1958/59 | Football League (1) | 30 August 1958 | Stamford Bridge | L | 2-6 | Stan Cullis | Ted Drake |
| 1958/59 | Football League (1) | 3 January 1959 | Molineux | L | 1-2 | Stan Cullis | Ted Drake |
| 1959/60 | Football League (1) | 28 November 1959 | Molineux | W | 3-1 | Stan Cullis | Ted Drake |
| 1959/60 | Football League (1) | 30 April 1960 | Stamford Bridge | W | 5-1 | Stan Cullis | Ted Drake |
| 1960/61 | Football League (1) | 27 August 1960 | Stamford Bridge | D | 3-3 | Stan Cullis | Ted Drake |
| 1960/61 | Football League (1) | 31 December 1960 | Molineux | W | 6-1 | Stan Cullis | Ted Drake |
| 1961/62 | Football League (1) | 20 April 1962 | Stamford Bridge | W | 5-4 | Stan Cullis | Tommy Docherty |
| 1961/62 | Football League (1) | 23 April 1962 | Molineux | D | 1-1 | Stan Cullis | Tommy Docherty |
| 1963/64 | Football League (1) | 28 September 1963 | Molineux | W | 4-1 | Stan Cullis | Tommy Docherty |
| 1963/64 | Football League (1) | 8 February 1964 | Stamford Bridge | W | 3-2 | Stan Cullis | Tommy Docherty |
| 1963/64 | Friendly | 21 May 1964 | Bridgetown | W | 3-1 | Stan Cullis | Tommy Docherty |
| 1963/64 | Friendly | 25 May 1964 | Port of Spain | L | 2-3 | Stan Cullis | Tommy Docherty |
| 1963/64 | Friendly | 27 May 1964 | Kingston | W | 4-2 | Stan Cullis | Tommy Docherty |
| 1963/64 | Friendly | 1 June 1964 | Kingston | L | 0-3 | Stan Cullis | Tommy Docherty |
| 1963/64 | Friendly | 5 June 1964 | Port-au-Prince | L | 0-2 | Stan Cullis | Tommy Docherty |
| 1964/65 | Football League (1) | 22 August 1964 | Molineux | L | 0-3 | Stan Cullis | Tommy Docherty |
| 1964/65 | Football League (1) | 12 December 1964 | Stamford Bridge | L | 1-2 | Andy Beattie © | Tommy Docherty |
| 1967/68 | Football League (1) | 29 April 1968 | Stamford Bridge | L | 0-1 | Ronnie Allen | Dave Sexton |
| 1967/68 | Football League (1) | 4 May 1968 | Molineux | W | 3-0 | Ronnie Allen | Dave Sexton |
| 1968/69 | Football League (1) | 12 October 1968 | Molineux | D | 1-1 | Ronnie Allen | Dave Sexton |
| 1968/69 | Football League (1) | 14 December 1968 | Stamford Bridge | D | 1-1 | Bill McGarry | Dave Sexton |
| 1969/70 | Football League (1) | 13 September 1969 | Stamford Bridge | D | 2-2 | Bill McGarry | Dave Sexton |
| 1969/70 | Football League (1) | 13 December 1969 | Molineux | W | 3-0 | Bill McGarry | Dave Sexton |
| 1970/71 | Football League (1) | 12 September 1970 | Stamford Bridge | D | 2-2 | Bill McGarry | Dave Sexton |
| 1970/71 | Football League (1) | 13 February 1971 | Molineux | W | 1-0 | Bill McGarry | Dave Sexton |
| 1971/72 | Football League (1) | 2 October 1971 | Stamford Bridge | L | 1-3 | Bill McGarry | Dave Sexton |
| 1971/72 | Football League (1) | 12 April 1972 | Molineux | L | 0-2 | Bill McGarry | Dave Sexton |
| 1972/73 | Football League (1) | 16 December 1972 | Molineux | W | 1-0 | Bill McGarry | Dave Sexton |
| 1972/73 | Football League (1) | 6 March 1973 | Stamford Bridge | W | 2-0 | Bill McGarry | Dave Sexton |
| 1973/74 | Football League (1) | 29 September 1973 | Stamford Bridge | D | 2-2 | Bill McGarry | Dave Sexton |
| 1973/74 | Football League (1) | 22 December 1973 | Molineux | W | 2-0 | Bill McGarry | Dave Sexton |
| 1974/75 | Football League (1) | 28 September 1974 | Stamford Bridge | W | 1-0 | Bill McGarry | Dave Sexton |
| 1974/75 | Football League (1) | 15 March 1975 | Molineux | W | 7-1 | Bill McGarry | Ron Suart |
| 1976/77 | Football League (2) | 11 December 1976 | Stamford Bridge | D | 3-3 | Sammy Chung | Eddie McCreadie |
| 1976/77 | Football League (2) | 07 May 1977 | Molineux | D | 1-1 | Sammy Chung | Eddie McCreadie |
| 1977/78 | Football League (1) | 10 December 1977 | Molineux | L | 1-3 | Sammy Chung | Ken Shellito |
| 1977/78 | Football League (1) | 22 April 1978 | Stamford Bridge | D | 1-1 | Sammy Chung | Ken Shellito |
| 1978/79 | Football League (1) | 22 August 1978 | Molineux | L | 0-1 | Sammy Chung | Ken Shellito |
| 1978/79 | Football League (1) | 24 March 1979 | Stamford Bridge | W | 2-1 | John Barnwell | Danny Blanchflower |
| 1982/83 | Football League (2) | 31 August 1982 | Stamford Bridge | D | 0-0 | Graham Hawkins | John Neal |
| 1982/83 | Football League (2) | 22 January 1983 | Molineux | W | 2-1 | Graham Hawkins | John Neal |
| 1990/91 | Friendly | 14 August 1990 | Molineux | D | 2-2 | Graham Turner | Bobby Campbell |
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