| First Team Matches | League Debut | Associated with both clubs | Transfers |
|
To Wolves |
||
| Marshall, GH | Fee Unknown | 14 May 1919 |
| Woodward, M | Fee Unknown | 1 April 1920 |
| Burrill, F | Fee Unknown | 14 May 1921 |
| Westley, SLM | £150,000 | 19 June 1989 |
| Eastwood, F | £2,000,000 | 6 July 2007 |
|
To Southend |
||
| Richardson, JT | Fee Unknown | 6 August 1930 |
| Hatfield, SE | Fee Unknown | 7 August 1931 |
| Smith, WC | Fee Unknown | 1 August 1933 |
| Deacon, J | Fee Unknown | 12 October 1934 |
| Thornhill, D | Fee Unknown | 25 March 1948 |
| Kellock, W | £20,000 | 1 September 1983 |
| Malone, SL | Loan | 1 August 2009 |
| Friend, G | Loan | 18 September 2009 |
| Cassidy, JA | Loan | 14 January 2015 |
