| First Team Matches | Second Team Matches | Youth Team Matches | League Debuts | Associated with both clubs | Transfers | Programmes |
| Order | Date | Player | Venue | Results | Extra Info | Season | |
| 314 | 17 December 1927 | Baxter, T | Stamford Bridge | L | 0-2 | 1927/28 | |
| 333 | 16 March 1929 | Rhodes, R | Stamford Bridge | W | 2-0 | 1928/29 | |
| 398 | 21 December 1935 | Curnow, J | Stamford Bridge | D | 2-2 | 1935/36 | |
| 411 | 13 March 1937 | Taylor, F | Stamford Bridge | W | 1-0 | 1936/37 | |
| 412 | 13 March 1937 | Coley, W | Stamford Bridge | W | 1-0 | 1936/37 | |
| 417 | 18 December 1937 | Smith, R | Stamford Bridge | W | 2-0 | 1937/38 | |
| 431 | 1 April 1939 | McDonald, J | Molineux | W | 2-0 | 1938/39 | |
| 525 | 23 April 1962 | Woodfield, D | Molineux | D | 1-1 | 1961/62 | |
| 533 | 22 August 1964 | Ford, C | Molineux | L | 0-3 | 1964/65 | |
| 562 | 29 April 1968 | McAlle, J | Stamford Bridge | L | 0-1 | 1967/68 | |
| 593 | 15 March 1975 | Carr, W | Molineux | W | 7-1 | 1g | 1974/75 |
| 602 | 7 May 1977 | Berry, G | Molineux | D | 1-1 | 1976/77 | |
| 631 | 31 August 1982 | Smith, G | Stamford Bridge | D | 0-0 | Sub | 1982/83 |
| 936 | 23 October 2010 | Hunt, S | Stamford Bridge | L | 0-2 | Sub | 2010/11 |
| 942 | 26 November 2011 | Forde, A | Stamford Bridge | L | 0-3 | Sub | 2011/12 |
| 943 | 2 January 2012 | Frimpong, E | Molineux | L | 1-2 | 2011/12 | |
| 1033 | 5 December 2018 | Dendoncker, L | Stamford Bridge | W | 2-1 | Sub | 2018/19 |
| 1037 | 14 September 2019 | Vallejo, J | Molineux | L | 2-5 | 2019/20 | |
| 1039 | 26 July 2020 | Jordoa, B | Stamford Bridge | L | 0-2 | Sub | 2019/20 |
| 1046 | 15 December 2020 | Otasowie, O | Molineux | W | 2-1 | Sub | 2020/21 |
| 1047 | 27 January 2021 | Willian, Jose | Stamford Bridge | D | 0-0 | Sub | 2020/21 |
| 1062 | 8 October 2022 | Hodge, J | Stamford Bridge | L | 0-3 | Sub | 2022/23 |
