| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers | Programmes |
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Chelsea Manager | |
| 1993/94 | FA Cup | 13 March 1994 | Stamford Bridge | L | 0-1 | Graham Turner | Glenn Hoddle |
| 1996/97 | Friendly | 31 July 1996 | Molineux | L | 0-1 | Mark McGhee | Ruud Gullit |
| 2003/04 | Premier League | 20 September 2003 | Molineux | L | 0-5 | Dave Jones | Claudio Ranieri |
| 2003/04 | Premier League | 27 March 2004 | Stamford Bridge | L | 2-5 | Dave Jones | Claudio Ranieri |
| 2009/10 | Premier League | 21 November 2009 | Stamford Bridge | L | 0-4 | Mick McCarthy | Carlo Ancelotti |
| 2009/10 | Premier League | 20 February 2010 | Molineux | L | 0-2 | Mick McCarthy | Carlo Ancelotti |
| 2010/11 | Premier League | 23 October 2010 | Stamford Bridge | L | 0-2 | Mick McCarthy | Carlo Ancelotti |
| 2010/11 | Premier League | 5 January 2011 | Molineux | W | 1-0 | Mick McCarthy | Carlo Ancelotti |
| 2011/12 | Premier League | 26 November 2011 | Stamford Bridge | L | 0-3 | Mick McCarthy | Andre Villas-Boas |
| 2011/12 | Premier League | 2 January 2012 | Molineux | L | 1-2 | Mick McCarthy | Roberto de Matteo |
| 2012/13 | FL Cup | 25 September 2012 | Stamford Bridge | L | 0-6 | Stole Solbakken | Roberto de Matteo |
| 2016/17 | FA Cup | 18 February 2017 | Molineux | L | 0-2 | Paul Lambert | Antonio Conte |
| 2018/19 | Premier League | 5 December 2018 | Molineux | W | 2-1 | Nuno Espirito Santo | Maurizio Sarri |
| 2018/19 | Premier League | 10 March 2019 | Stamford Bridge | D | 1-1 | Nuno Espirito Santo | Maurizio Sarri |
| 2019/20 | Premier League | 14 September 2019 | Molineux | L | 2-5 | Nuno Espirito Santo | Frank Lampard |
| 2019/20 | Premier League | 26 July 2020 | Stamford Bridge | L | 0-2 | Nuno Espirito Santo | Frank Lampard |
| 2020/21 | Premier League | 15 December 2020 | Molineux | W | 2-1 | Nuno Espirito Santo | Frank Lampard |
| 2020/21 | Premier League | 27 January 2021 | Stamford Bridge | D | 0-0 | Nuno Espirito Santo | Thomas Tuchel* |
| 2021/22 | Premier League | 19 December 2021 | Molineux | D | 0-0 | Bruna Lage | Thomas Tuchel |
| 2021/22 | Premier League | 7 May 2022 | Stamford Bridge | L | 0-2 | Bruna Lage | Thomas Tuchel |
| 2022/23 | Premier League | 8 October 2022 | Stamford Bridge | L | 0-3 | Steve Davis © | Graham Potter |
| 2022/23 | Premier League | 8 April 2023 | Molineux | W | 1-0 | Julen Lopetegui | Frank Lampard* |
| 2023/24 | Premier League | 23 December 2023 | Molineux | W | 2-1 | Gary O’Neil | Mauricio Pochettino |
| 2023/24 | Premier League | 4 February 2024 | Stamford Bridge | W | 4-2 | Gary O’Neil | Mauricio Pochettino |
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