| Club | Results | Competition | Date | Venue | Wolves Manager | |
| Lincoln City | W | 4-0 | Football League (2) | 20 October 1906 | Sincil Bank | Jack Addenbrooke |
| Lincoln City | W | 3-0 | Football League (2) | 23 February 1907 | Molineux | Jack Addenbrooke |
| Chelsea | L | 0-2 | Football League (2) | 24 September 1910 | Stamford Bridge | Jack Addenbrooke |
| Chelsea | D | 0-0 | Football League (2) | 28 January 1911 | Molineux | Jack Addenbrooke |
| Chelsea | L | 0-2 | FA Cup | 25 February 1911 | Molineux | Jack Addenbrooke |
| Chelsea | L | 0-4 | Football League (2) | 16 September 1911 | Stamford Bridge | Jack Addenbrooke |
| Chelsea | W | 3-1 | Football League (2) | 20 January 1912 | Molineux | Jack Addenbrooke |
| Chelsea | L | 0-1 | Football League (2) | 25 December 1924 | Stamford Bridge | Albert Hoskins |
| Chelsea | L | 0-1 | Football League (2) | 26 December 1924 | Molineux | Albert Hoskins |
| Chelsea | D | 0-0 | Football League (2) | 14 November 1925 | Molineux | Albert Hoskins |
| Chelsea | D | 3-3 | Football League (2) | 27 March 1926 | Stamford Bridge | Fred Scotchbrook |
| Chelsea | L | 0-3 | Football League (2) | 30 August 1926 | Molineux | Fred Scotchbrook |
| Chelsea | L | 0-1 | Football League (2) | 18 April 1927 | Stamford Bridge | Fred Scotchbrook |
| Chelsea | L | 0-2 | Football League (2) | 17 December 1927 | Stamford Bridge | Major Frank Buckley |
| Chelsea | W | 2-1 | FA Cup | 14 January 1928 | Molineux | Major Frank Buckley |
| Chelsea | L | 1-2 | Football League (2) | 28 April 1928 | Molineux | Major Frank Buckley |
| Chelsea | D | 1-1 | Football League (2) | 3 November 1928 | Molineux | Major Frank Buckley |
| Chelsea | W | 2-0 | Football League (2) | 16 March 1929 | Stamford Bridge | Major Frank Buckley |
| Chelsea | D | 1-1 | Football League (2) | 23 November 1929 | Stamford Bridge | Major Frank Buckley |
| Chelsea | L | 0-1 | Football League (2) | 29 March 1930 | Molineux | Major Frank Buckley |
| Chelsea | L | 1-2 | Football League (1) | 17 September 1932 | Molineux | Major Frank Buckley |
| Chelsea | L | 1-3 | Football League (1) | 28 January 1933 | Stamford Bridge | Major Frank Buckley |
