| Seasons | Competitions | Date | Venue | | Results | Wolves Manager | Middlesbrough Manager | Referee |
| 1888/89 | Friendly | 24 Apr 1889 | Linthorpe Road | W | 5-2 | Jack Addenbrooke | | x |
| 1892/93 | FA Cup | 4 February 1893 | Molineux | W | 2-1 | Jack Addenbrooke | | J Fox (Sheffield) |
| 1902/03 | Football League (1) | 25 October 1902 | Linthorpe Road | L | 0-2 | Jack Addenbrooke | John Robson | F Bye (Sheffield) |
| 1902/03 | Football League (1) | 26 December 1902 | Molineux | W | 2-0 | Jack Addenbrooke | John Robson | AJ Barker (Hanley) |
| 1903/04 | Football League (1) | 28 November 1903 | Ayresome Park | W | 2-1 | Jack Addenbrooke | John Robson | F Bye (Sheffield) |
| 1903/04 | Football League (1) | 26 March 1904 | Molineux | D | 2-2 | Jack Addenbrooke | John Robson | F Bye (Sheffield) |
| 1904/05 | Football League (1) | 26 November 1904 | Molineux | W | 5-3 | Jack Addenbrooke | John Robson | T Armitt (Leek) |
| 1904/05 | Football League (1) | 25 March 1905 | Ayresome Park | L | 1-3 | Jack Addenbrooke | John Robson | J Howcroft (Bolton) |
| 1905/06 | Football League (1) | 14 October 1905 | Ayresome Park | L | 1-3 | Jack Addenbrooke | Alex Massie | A Sutcliffe (Burnley) |
| 1905/06 | Football League (1) | 17 February 1906 | Molineux | D | 0-0 | Jack Addenbrooke | Alex Massie | A Sutcliffe (Burnley) |
| 1924/25 | Football League (2) | 10 September 1924 | Ayresome Park | L | 0-2 | Albert Hoskins | Herbert Bamlett | E Wood (Sheffield) |
| 1924/25 | Football League (2) | 2 May 1925 | Molineux | W | 1-0 | Albert Hoskins | Herbert Bamlett | E Wood (Sheffield) |
| 1925/26 | Football League (2) | 5 September 1925 | Ayresome Park | L | 1-4 | Albert Hoskins | Herbert Bamlett | T Brown (Lincoln) |
| 1925/26 | Football League (2) | 16 January 1926 | Molineux | W | 3-1 | Albert Hoskins | Herbert Bamlett | T Brown (Lincoln) |
| 1926/27 | Football League (2) | 25 September 1926 | Molineux | L | 1-2 | Fred Scotchbrook | Herbert Bamlett | R Collinge (Manchester) |
| 1926/27 | Football League (2) | 12 February 1927 | Ayresome Park | L | 0-2 | Fred Scotchbrook | Peter McWilliam | R Collinge (Manchester) |
| 1928/29 | Football League (2) | 29 September 1928 | Molineux | D | 3-3 | Major Frank Buckley | Peter McWilliam | A Fogg (Bolton) |
| 1928/29 | Football League (2) | 9 February 1929 | Ayresome Park | L | 3-8 | Major Frank Buckley | Peter McWilliam | A Fogg (Bolton) |
| 1932/33 | Football League (1) | 14 April 1933 | Molineux | W | 2-0 | Major Frank Buckley | Peter McWilliam | E Wood (Sheffield) |
| 1932/33 | Football League (1) | 17 April 1933 | Ayresome Park | L | 1-2 | Major Frank Buckley | Peter McWilliam | E Wood (Sheffield) |
| 1933/34 | Football League (1) | 25 November 1933 | Molineux | L | 0-1 | Major Frank Buckley | Peter McWilliam | H Hartley (Bolton) |
| 1933/34 | Football League (1) | 7 April 1934 | Ayresome Park | D | 0-0 | Major Frank Buckley | Wilf Gillow | H Hartley (Bolton) |
| 1934/35 | Football League (1) | 17 November 1934 | Ayresome Park | D | 2-2 | Major Frank Buckley | Wilf Gillow | C Fletcher (Davenham) |
| 1934/35 | Football League (1) | 30 March 1935 | Molineux | W | 5-3 | Major Frank Buckley | Wilf Gillow | J Mellor (Bradford) |
| 1935/36 | Football League (1) | 18 September 1935 | Ayresome Park | L | 2-4 | Major Frank Buckley | Wilf Gillow | T Bentley (Chorlton cum Hardy) |
| 1935/36 | Football League (1) | 2 May 1936 | Molineux | W | 4-0 | Major Frank Buckley | Wilf Gillow | A Taylor (Wigan) |
| 1936/37 | Football League (1) | 31 August 1936 | Molineux | L | 0-1 | Major Frank Buckley | Wilf Gillow | R Warburton (Bolton) |
| 1936/37 | Football League (1) | 09 September 1936 | Ayresome Park | L | 0-1 | Major Frank Buckley | Wilf Gillow | R Warburton (Bolton) |
| 1936/37 | FA Cup | 16 January 1937 | Molineux | W | 6-1 | Major Frank Buckley | Wilf Gillow | H Mee (Mansfield) |
| 1937/38 | Football League (1) | 23 March 1938 | Molineux | L | 0-1 | Major Frank Buckley | Wilf Gillow | T Bentley (Chorlton cum Hardy) |
| 1937/38 | Football League (1) | 23 April 1938 | Ayresome Park | W | 3-0 | Major Frank Buckley | Wilf Gillow | T Bentley (Chorlton cum Hardy) |
| 1938/39 | Football League (1) | 29 October 1938 | Ayresome Park | L | 0-1 | Major Frank Buckley | Wilf Gillow | J Hargreaves (Preston) |
| 1938/39 | Football League (1) | 8 March 1939 | Molineux | W | 6-1 | Major Frank Buckley | Wilf Gillow | J Hargreaves (Preston) |
| 1946/47 | Football League (1) | 2 November 1946 | Molineux | L | 2-4 | Ted Vizard | David Jack | H Hartley (Bolton) |
| 1946/47 | Football League (1) | 8 March 1947 | Ayresome Park | D | 1-1 | Ted Vizard | David Jack | H Hartley (Bolton) |
| 1947/48 | Football League (1) | 10 September 1947 | Molineux | L | 1-3 | Ted Vizard | David Jack | H Jackson (Leeds) |
| 1947/48 | Football League (1) | 1 January 1948 | Ayresome Park | W | 4-2 | Ted Vizard | David Jack | H Jackson (Leeds) |
| 1948/49 | Football League (1) | 9 October 1948 | Molineux | L | 0-3 | Stan Cullis | David Jack | R Mortimer (Huddersfield) |
| 1948/49 | Football League (1) | 5 March 1949 | Ayresome Park | D | 4-4 | Stan Cullis | David Jack | R Mortimer (Huddersfield) |
| 1949/50 | Football League (1) | 10 September 1949 | Molineux | W | 3-1 | Stan Cullis | David Jack | F Coutas (Hull) |
| 1949/50 | Football League (1) | 14 January 1950 | Ayresome Park | L | 0-2 | Stan Cullis | David Jack | F Coutas (Hull) |
| 1950/51 | Football League (1) | 7 October 1950 | Molineux | L | 3-4 | Stan Cullis | David Jack | J Clough (Bolton) |
| 1950/51 | Football League (1) | 11 April 1951 | Ayresome Park | W | 2-1 | Stan Cullis | David Jack | J Clough (Bolton) |
| 1951/52 | Football League (1) | 8 December 1951 | Molineux | W | 4-0 | Stan Cullis | David Jack | A Ellis (Halifax) |
| 1951/52 | Football League (1) | 26 April 1952 | Ayresome Park | L | 0-4 | Stan Cullis | Committee | A Ellis (Halifax) |
| 1952/53 | Football League (1) | 25 October 1952 | Molineux | D | 3-3 | Stan Cullis | Walter Rowley | T Seymour (Wakefield) |
| 1952/53 | Football League (1) | 14 March 1953 | Ayresome Park | D | 1-1 | Stan Cullis | Walter Rowley | T Seymour (Wakefield) |
| 1953/54 | Football League (1) | 7 November 1953 | Ayresome Park | D | 3-3 | Stan Cullis | Walter Rowley | R Hartley (Burnley) |
| 1953/54 | Football League (1) | 27 March 1954 | Molineux | L | 2-4 | Stan Cullis | Committee | R Hartley (Burnley) |
