| Date | Opponents | Venue | Competition | Results |
David Calderhead ‘jnr’
| 24 September 1910 | Chelsea | Stamford Bridge | Football League (2) | L | 0-2 |
| 28 January 1911 | Chelsea | Molineux | Football League (2) | D | 0-0 |
| 25 February 1911 | Chelsea | Molineux | FA Cup | L | 0-2 |
| 16 September 1911 | Chelsea | Stamford Bridge | Football League (2) | L | 0-4 |
| 20 January 1912 | Chelsea | Molineux | Football League (2) | W | 3-1 |
David Calderhead ‘snr’
| 20 October 1906 | Lincoln City | Sincil Bank | Football League (2) | W | 4-0 |
| 23 February 1907 | Lincoln City | Molineux | Football League (2) | W | 3-0 |
William Cameron
| 11 October 1919 | Bury | Gigg Lane | Football League (2) | L | 0-2 |
| 18 October 1919 | Bury | Molineux | Football League (2) | L | 0-1 |
| 11 September 1920 | Bury | Molineux | Football League (2) | W | 2-1 |
| 18 September 1920 | Bury | Gigg Lane | Football League (2) | L | 1-3 |
| 14 April 1922 | Bury | Gigg Lane | Football League (2) | L | 1-2 |
| 17 April 1922 | Bury | Molineux | Football League (2) | D | 1-1 |
Bob Campbell
| 3 October 1896 | Sunderland | Newcastle Road | Football League (1) | W | 3-0 |
| 24 October 1896 | Sunderland | Molineux | Football League (1) | L | 0-1 |
| 11 September 1897 | Sunderland | Newcastle Road | Football League (1) | L | 2-3 |
| 13 November 1897 | Sunderland | Molineux | Football League (1) | W | 4-2 |
| 5 November 1898 | Sunderland | Molineux | Football League (1) | W | 2-0 |
| 4 March 1899 | Sunderland | Roker Park | Football League (1) | L | 0-3 |
Harry Chapman
| 19 April 1913 | Hull City | Molineux | Football League (2) | L | 0-1 |
| 6 December 1913 | Hull City | Anlaby Road | Football League (2) | L | 1-7 |
| 11 April 1914 | Hull City | Molineux | Football League (2) | W | 1-0 |
Herbert Chapman
| 28 September 1912 | Leeds City | Elland Road | Football League (2) | D | 2-2 |
| 25 January 1913 | Leeds City | Molineux | Football League (2) | D | 2-2 |
| 11 October 1913 | Leeds City | Molineux | Football League (2) | L | 1-3 |
| 14 February 1914 | Leeds City | Elland Road | Football League (2) | L | 0-5 |
| 5 April 1915 | Leeds City | Molineux | Football League (2) | W | 5-1 |
| 6 April 1915 | Leeds City | Elland Road | Football League (2) | W | 3-2 |
| 27 September 1919 | Leeds City | Elland Road | Football League (2) | D | 1-1 |
| 4 October 1919 | Leeds City | Molineux | Football League (2) | L | 2-4 |
Tom Clare
| 10 November 1906 | Burslem Port Vale | Molineux | Football League (2) | W | 6-2 |
| 16 March 1907 | Burslem Port Vale | Athletic Ground | Football League (2) | D | 0-0 |
John Cox
| 4 September 1909 | Blackpool | Bloomfield Road | Football League (2) | L | 0-2 |
| 8 January 1910 | Blackpool | Molineux | Football League (2) | W | 2-1 |
| 8 October 1910 | Blackpool | Bloomfield Road | Football League (2) | L | 0-2 |
| 11 February 1911 | Blackpool | Molineux | Football League (2) | L | 0-3 |
| 21 October 1911 | Blackpool | Molineux | Football League (2) | W | 3-0 |
Tommy Crawshaw
| 28 November 1914 | Glossop | Molineux | Football League (2) | W | 4-0 |
| 3 April 1915 | Glossop | North Road | Football League (2) | W | 2-0 |
William C Cuff
| 7 September 1901 | Everton | Goodison Park | Football League (1) | L | 1-6 |
| 26 December 1901 | Everton | Molineux | Football League (1) | W | 2-1 |
| 20 September 1902 | Everton | Molineux | Football League (1) | D | 1-1 |
| 17 January 1903 | Everton | Goodison Park | Football League (1) | L | 1-2 |
| 5 December 1903 | Everton | Molineux | Football League (1) | D | 2-2 |
| 2 April 1904 | Everton | Goodison Park | Football League (1) | L | 0-2 |
| 8 October 1904 | Everton | Goodison Park | Football League (1) | L | 1-2 |
| 26 December 1904 | Everton | Molineux | Football League (1) | L | 0-3 |
| 2 December 1905 | Everton | Molineux | Football League (1) | L | 2-5 |
| 7 April 1906 | Everton | Goodison Park | Football League (1) | D | 2-2 |
