Player Transfers: 1999-00
| Player Arriving | |
| Player Leaving |
| Date | Player | Club | Fee | |
|---|---|---|---|---|
| 30 Jun 2000 | Alessandro Pistone | Newcastle | £3m | |
| 13 Jun 2000 | Carl Regan | Barnsley | Free | |
| 25 May 2000 | Adam Farley | Released | Free | |
| 26 Apr 2000 | Dean Delaney | Released; Port Vale | Free | |
| 26 Apr 2000 | George Dempsey | Released | Free | |
| 26 Apr 2000 | David Knowles | Released | Free | |
| 14 Mar 2000 | Mark Hughes | Southampton | Free | |
| 7 Mar 2000 | Stephen Hughes | Arsenal | £500k | |
| 29 Feb 2000 | Slaven Bilic | Retired; Hajduk Split (Cro) | Free | |
| 2 Feb 2000 | Terry Phelan | Fulham | Free | |
| 10 Jan 2000 | Michael Branch | Wolves | £500k | |
| 24 Dec 1999 | Tony Grant | Manchester City | £450k | |
| 23 Dec 1999 | John O'Kane | Bolton Wanderers | Free | |
| 17 Dec 1999 | Gareth Farrelly | Bolton Wanderers | £400k | |
| 13 Nov 1999 | Joe-Max Moore | New England Rev (USA) | Free | |
| 3 Sep 1999 | Abel Xavier | PSV Eindhoven (Hol) | £1.5m | |
| 5 Aug 1999 | John Oster | Sunderland | £1.1m | |
| 5 Aug 1999 | Mark Pembridge | Benfica | £800k | |
| 2 Aug 1999 | Craig Short | Blackburn Rovers | £2.1m | |
| 13 Jul 1999 | Kevin Campbell | Trabsonspor | £3m | |
| 13 Jul 1999 | Kevin Campbell | Trabsonspor | £3m | |
| 8 Jul 1999 | Marco Materazzi | Perugia | £3m |
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