Players in
| Player | From | Fee | Date |
| Stefan Malz | 1860 Munich | £ 650000 | 24-06-1999 |
| Sylvinho | Corinthians (Old) | £ 4000000 | 30-06-1999 |
| Davor Suker | Real Madrid | £ 500000 | 02-08-1999 |
| Thierry Henry | Juventus | £ 10500000 | 03-08-1999 |
| Niccolo Galli | Fiorentina | | 06-08-1999 |
| Lauren | Mallorca | £ 7200000 | 30-05-2000 |
| Total: £ 22850000 | |||
Players out | |||
| Player | To | Fee | Date |
| Steve Bould | Sunderland | £ 500000 | 02-07-1999 |
| Jason Crowe | Portsmouth | £ 1000000 | 07-07-1999 |
| Michael Black | Tranmere | Free | 07-07-1999 |
| Nicolas Anelka | Real Madrid | £ 23000000 | 02-08-1999 |
| Dave Livermore | Millwall | £ 30000 | 02-08-1999 |
| Luis Boa Morte | Southampton | £ 500000 | 25-08-1999 |
| Omer Riza | West Ham | Nominal | 02-12-1999 |
| Stephen Hughes | Everton | £ 3000000 | 07-03-2000 |
| Narada Bernard | Bournemouth | Free | 07-06-2000 |
| Nigel Winterburn | West Ham | Signed | 22-06-2000 |
| Davor Suker | West Ham | Free | 28-06-2000 |
| Tommy Black | C Palace | £ 500000 | 01-07-2000 |
| Julian Gray | C Palace | £ 500000 | 01-07-2000 |
| Total: £ 29030000 | |||
Loans (players in) | |||
| Player | From | Start | End |
Loans (players out) | |||
| Player | To | Start | End |
| Stephen Hughes | Fulham | 23-07-1999 | 30-08-1999 |
| Tommy Black | Carlisle | 27-08-1999 | 29-09-1999 |
| Alberto Mendez | Unterhaching | 17-09-1999 | |
| Stuart Taylor | Bristol R | 23-09-1999 | 23-10-1999 |
| Tommy Black | Bristol C | 17-12-1999 | 04-01-2000 |
| Brian McGovern | QPR | 26-12-1999 | 01-02-2000 |
| Paolo Vernazza | Portsmouth | 13-01-2000 | 03-03-2000 |
| Nelson Vivas | Celta Vigo | 17-01-2000 | |
| Ashley Cole | C Palace | 25-02-2000 | 08-05-2000 |
| David Grondin | Cannes | 01-07-2000 | 31-05-2002 |
Released players | |||
| Player | Date | ||
| Remi Garde | 10-06-1999 | ||
Source : Soccer Base
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