| Seasons | Competition | Date | Venue | | Results | Wolves Manager | Bolton Manager | Referee |
| 1937/38 | Football League (1) | 25 September 1937 | Molineux | D | 1-1 | Major Frank Buckley | Charles Foweraker | S Boardman (Hale) |
| 1937/38 | Football League (1) | 5 February 1938 | Burnden Park | W | 2-1 | Major Frank Buckley | Charles Foweraker | S Boardman (Hale) |
| 1938/39 | Football League (1) | 17 December 1938 | Molineux | D | 1-1 | Major Frank Buckley | Charles Foweraker | G Salmon (Stoke on Trent) |
| 1938/39 | Football League (1) | 22 April 1939 | Burnden Park | D | 0-0 | Major Frank Buckley | Charles Foweraker | G Salmon (Stoke on Trent) |
| 1944/45 | War Competition | 5 May 1945 | Molineux | D | 2-2 | Ted Vizard | Walter Rowley | HT Wright (Macclesfield) |
| 1944/45 | War Competition | 12 May 1945 | Burnden Park | L | 1-2 | Ted Vizard | Walter Rowley | Unknown |
| 1946/47 | Football League (1) | 14 December 1946 | Molineux | W | 5-0 | Ted Vizard | Walter Rowley | G Salmon (Stoke on Trent) |
| 1946/47 | Football League (1) | 19 April 1947 | Burnden Park | W | 3-0 | Ted Vizard | Walter Rowley | HT Wright (Macclesfield) |
| 1947/48 | Football League (1) | 6 December 1947 | Burnden Park | L | 2-3 | Ted Vizard | Walter Rowley | HT Wright (Macclesfield) |
| 1947/48 | Football League (1) | 24 April 1948 | Molineux | W | 1-0 | Ted Vizard | Walter Rowley | HT Wright (Macclesfield) |
| 1948/49 | Football League (1) | 28 August 1948 | Burnden Park | W | 5-0 | Stan Cullis | Walter Rowley | HT Wright (Macclesfield) |
| 1948/49 | Football League (1) | 1 January 1949 | Molineux | W | 2-0 | Stan Cullis | Walter Rowley | HT Wright (Macclesfield) |
| 1949/50 | Football League (1) | 10 December 1949 | Molineux | D | 1-1 | Stan Cullis | Walter Rowley | L Thompson (Worksop) |
| 1949/50 | Football League (1) | 29 April 1950 | Burnden Park | W | 4-2 | Stan Cullis | Walter Rowley | L Thompson (Worksop) |
| 1950/51 | Football League (1) | 2 September 1950 | Molineux | W | 7-1 | Stan Cullis | Walter Rowley | A Murdoch (Sheffield) |
| 1950/51 | Football League (1) | 28 April 1951 | Burnden Park | L | 1-2 | Stan Cullis | Bill Ridding | A Murdoch (Sheffield) |
| 1951/52 | Football League (1) | 13 October 1951 | Molineux | W | 5-1 | Stan Cullis | Bill Ridding | A Murdoch (Sheffield) |
| 1951/52 | Football League (1) | 1 March 1952 | Burnden Park | D | 2-2 | Stan Cullis | Bill Ridding | A Murdoch (Sheffield) |
| 1952/53 | Football League (1) | 25 August 1952 | Molineux | W | 3-1 | Stan Cullis | Bill Ridding | J Ball (Seaton Delaval) |
| 1952/53 | Football League (1) | 1 September 1952 | Burnden Park | L | 1-2 | Stan Cullis | Bill Ridding | J Ball (Seaton Delaval) |
| 1953/54 | Football League (1) | 24 October 1953 | Burnden Park | D | 1-1 | Stan Cullis | Bill Ridding | W Ratcliffe (Leek) |
| 1953/54 | Football League (1) | 24 March 1954 | Molineux | D | 1-1 | Stan Cullis | Bill Ridding | W Ratcliffe (Leek) |
| 1954/55 | Football League (1) | 18 September 1954 | Molineux | L | 1-2 | Stan Cullis | Bill Ridding | S Rogers (Shrewsbury) |
| 1954/55 | Football League (1) | 5 February 1955 | Burnden Park | L | 1-6 | Stan Cullis | Bill Ridding | S Rogers (Shrewsbury) |
| 1955/56 | Football League (1) | 1 October 1955 | Burnden Park | L | 1-2 | Stan Cullis | Bill Ridding | L Howarth (Beverley) |
| 1955/56 | Football League (1) | 11 February 1956 | Molineux | W | 4-2 | Stan Cullis | Bill Ridding | L Howarth (Beverley) |
| 1956/57 | Football League (1) | 22 September 1956 | Burnden Park | W | 3-0 | Stan Cullis | Bill Ridding | R Windle (Chesterfield) |
| 1956/57 | Football League (1) | 2 February 1957 | Molineux | W | 3-2 | Stan Cullis | Bill Ridding | R Windle (Chesterfield) |
| 1957/58 | Football League (1) | 28 August 1957 | Molineux | W | 6-1 | Stan Cullis | Bill Ridding | G Pullin (Bristol) |
| 1957/58 | Football League (1) | 4 September 1957 | Burnden Park | D | 1-1 | Stan Cullis | Bill Ridding | L Howarth (Beverley) |
| 1957/58 | FA Cup | 1 March 1958 | Burnden Park | L | 1-2 | Stan Cullis | Bill Ridding | A Holland (Barnsley) |
| 1958/59 | Charity Shield | 6 October 1958 | Burnden Park | L | 1-4 | Stan Cullis | Bill Ridding | A Holland (Barnsley) |
| 1958/59 | Football League (1) | 22 November 1958 | Molineux | L | 1-2 | Stan Cullis | Bill Ridding | G Pullin (Bristol) |
| 1958/59 | FA Cup | 24 January 1959 | Molineux | L | 1-2 | Stan Cullis | Bill Ridding | A Ellis (Halifax) |
| 1958/59 | Football League (1) | 11 April 1959 | Burnden Park | D | 2-2 | Stan Cullis | Bill Ridding | J Topliss (Grimsby) |
| 1959/60 | Football League (1) | 26 December 1959 | Burnden Park | L | 1-2 | Stan Cullis | Bill Ridding | H Webb (Leeds) |
| 1959/60 | Football League (1) | 28 December 1959 | Molineux | L | 0-1 | Stan Cullis | Bill Ridding | J Finney (Wellington, Herf) |
| 1960/61 | Football League (1) | 24 August 1960 | Burnden Park | W | 2-0 | Stan Cullis | Bill Ridding | J Powell (Swinton) |
| 1960/61 | Football League (1) | 31 August 1960 | Molineux | W | 3-1 | Stan Cullis | Bill Ridding | R Smith (Newport, Mon) |
| 1961/62 | Football League (1) | 21 October 1961 | Burnden Park | L | 0-1 | Stan Cullis | Bill Ridding | R Harper (Sheffield) |
| 1961/62 | Football League (1) | 10 March 1962 | Molineux | W | 5-1 | Stan Cullis | Bill Ridding | P Rhodes (York) |
| 1962/63 | Football League (1) | 13 October 1962 | Burnden Park | L | 0-3 | Stan Cullis | Bill Ridding | H Wilson (Stockton on Tees) |
| 1962/63 | Football League (1) | 20 March 1963 | Molineux | W | 4-0 | Stan Cullis | Bill Ridding | L Callaghan (Merthyr Tydfil) |
| 1963/64 | Football League (1) | 19 October 1963 | Molineux | D | 2-2 | Stan Cullis | Bill Ridding | D Smith (Stonehouse, Glos) |
| 1963/64 | Football League (1) | 24 April 1964 | Burnden Park | W | 4-0 | Stan Cullis | Bill Ridding | W Holian (Chesterfield) |
| 1965/66 | Football League (2) | 4 December 1965 | Burnden Park | L | 1-2 | Andy Beattie © | Bill Ridding | H Hackney (Barnsley) |
| 1965/66 | Football League (2) | 30 April 1966 | Molineux | W | 3-1 | Andy Beattie © | Bill Ridding | P Rhodes (York) |
| 1966/67 | Football League (2) | 24 September 1966 | Burnden Park | D | 0-0 | Ronnie Allen | Bill Ridding | GW Hill (Scunthorpe) |
| 1966/67 | Football League (2) | 4 February 1967 | Molineux | W | 5-2 | Ronnie Allen | Bill Ridding | I Jones (Treharris) |
