| Player | Team | Date | Fee |
| Massimo Maccarone | Empoli | July 2002 | £8.15m |
| Ugo Ehiogu | Aston Villa | October 2000 | £8m |
| Fabrizio Ravanelli | Juventus | July 1996 | £7m |
| Gareth Southgate | Aston Villa | July 2001 | £6.5m |
| Nick Barmby | Tottenham | August 1995 | £5.25m |
| George Boateng | Aston Villa | August 2002 | £5m |
| Juninho | Sao Paulo | October 1995 | £4.75m |
| Paul Merson | Arsenal | July 1997 | £4.5m |
| Emerson | Porto | May 1996 | £4m |
| Christian Ziege | AC Milan | July 1999 | £4m |
| Juninho | Atletico Madrid | August 2002 | £3.8m |
| Paul Gascoigne | Rangers | March 1998 | £3.45m |
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