| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers |
| Competition | Date | Venue | Results | ||
| 1993/94 | FA Cup | 13 March 1994 | Stamford Bridge | L | 0-1 |
| 1996/97 | Friendly | 31 July 1996 | Molineux | L | 0-1 |
| 2003/04 | Premier League | 20 September 2003 | Molineux | L | 0-5 |
| 2003/04 | Premier League | 27 March 2004 | Stamford Bridge | L | 2-5 |
| 2009/10 | Premier League | 21 November 2009 | Stamford Bridge | L | 0-4 |
| 2009/10 | Premier League | 20 February 2010 | Molineux | L | 0-2 |
| 2010/11 | Premier League | 23 October 2010 | Stamford Bridge | L | 0-2 |
| 2010/11 | Premier League | 5 January 2011 | Molineux | W | 1-0 |
| 2011/12 | Premier League | 26 November 2011 | Stamford Bridge | L | 0-3 |
| 2011/12 | Premier League | 2 January 2012 | Molineux | L | 1-2 |
| 2012/13 | FL Cup | 25 September 2012 | Stamford Bridge | L | 0-6 |
| 2016/17 | FA Cup | 18 February 2017 | Molineux | L | 0-2 |
| 2018/19 | Premier League | 5 December 2018 | Molineux | W | 2-1 |
| 2018/19 | Premier League | 10 March 2019 | Stamford Bridge | D | 1-1 |
| 2019/20 | Premier League | 14 September 2019 | Molineux | L | 2-5 |
| 2019/20 | Premier League | 26 July 2020 | Stamford Bridge | L | 0-2 |
| 2020/21 | Premier League | 15 December 2020 | Molineux | W | 2-1 |
| 2020/21 | Premier League | 27 January 2021 | Stamford Bridge | D | 0-0 |
| 2021/22 | Premier League | 19 December 2021 | Molineux | D | 0-0 |
| 2021/22 | Premier League | 7 May 2022 | Stamford Bridge | L | 0-2 |
|