| Player | Club | Fee | Date |
|---|---|---|---|
| Sami Hyypia | Willem II | £2,500,000 | 19 May 1999 |
| Vladimir Smicer | Lens | £3,750,000 | 24 May 1999 |
| Titi Camara | Marseille | £2,600,000 | 1 June 1999 |
| Stephane Henchoz | Blackburn Rovers | £3,500,000 | 3 June 1999 |
| Sander Westerveld | Vitesse Arnhem | £4,000,000 | 15 June 1999 |
| Erik Meijer | Free Transfer | Free | 1 July 1999 |
| Didi Hamann | Newcastle United | £8,000,000 | 22 July 1999 |
| Emile Heskey | Leicester City | £11,000,000 | 10 March 2000 |
| Player | Club | Fee | Date |
|---|---|---|---|
| Rob Jones | West Ham United | Free | 27 May 1999 |
| Gareth Roberts | Panionios | £50,000 | 1 June 1999 |
| David James | Aston Villa | £1,800,000 | 17 June 1999 |
| Steve McManaman | Real Madrid | Free | 1 July 1999 |
| Tony Warner | Millwall | Free | 1 July 1999 |
| Jean Michel Ferri | Sochaux | £1,500,000 | 14 July 1999 |
| Jamie Cassidy | Cambridge United | Free | 22 July 1999 |
| Paul Ince | Middlesbrough | £1,000,000 | 30 July 1999 |
| Sean Dundee | VfB Stuttgart | £1,500,000 | 30 July 1999 |
| Øyvind Leonhardsen | Tottenham Hotspur | £2,800,000 | 6 August 1999 |
| Bjørn Tore Kvarme | Saint-Étienne | £750,000 | 30 August 1999 |
| Karl-Heinz Riedle | Fulham | £200,000 | 28 September 1999 |
| Pos | Team | Pld | Pts | GD | W | D | L | F | A |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Manchester United | 38 | 91 | +52 | 28 | 7 | 3 | 97 | 45 |
| 2 | Arsenal | 38 | 73 | +30 | 22 | 7 | 9 | 73 | 43 |
| 3 | Leeds United | 38 | 69 | +15 | 21 | 6 | 11 | 58 | 43 |
| 4 | Liverpool | 38 | 67 | +21 | 19 | 10 | 9 | 51 | 30 |
| 5 | Chelsea | 38 | 65 | +19 | 18 | 11 | 9 | 53 | 34 |
| 6 | Aston Villa | 38 | 58 | +11 | 15 | 13 | 10 | 46 | 35 |
| 7 | Sunderland | 38 | 58 | +1 | 16 | 10 | 12 | 57 | 56 |
| 8 | Leicester City | 38 | 55 | 0 | 16 | 7 | 15 | 55 | 55 |
| 9 | West Ham United | 38 | 55 | -1 | 15 | 10 | 13 | 52 | 53 |
| 10 | Tottenham Hotspur | 38 | 53 | +8 | 15 | 8 | 15 | 57 | 49 |
| 11 | Newcastle United | 38 | 52 | +9 | 14 | 10 | 14 | 63 | 54 |
| 12 | Middlesbrough | 38 | 52 | -6 | 14 | 10 | 14 | 46 | 52 |
| 13 | Everton | 38 | 50 | +10 | 12 | 14 | 12 | 59 | 49 |
| 14 | Coventry City | 38 | 44 | -7 | 12 | 8 | 18 | 47 | 54 |
| 15 | Southampton | 38 | 44 | -17 | 12 | 8 | 18 | 45 | 62 |
| 16 | Derby County | 38 | 38 | -13 | 9 | 11 | 18 | 44 | 57 |
| 17 | Bradford City | 38 | 36 | -30 | 9 | 9 | 20 | 38 | 68 |
| 18 | Wimbledon | 38 | 33 | -28 | 7 | 12 | 19 | 46 | 74 |
| 19 | Sheffield Wednesday | 38 | 31 | -32 | 8 | 7 | 23 | 38 | 70 |
| 20 | Watford | 38 | 24 | -42 | 6 | 6 | 26 | 35 | 77 |
| # | Date | Result | Opponent | Competition | |
|---|---|---|---|---|---|
| 1 | 07/08/1999 | 2 - 1 | Sheffield Wednesday | Premier League | |
| 2 | 14/08/1999 | 0 - 1 | Watford | Premier League | |
| 3 | 21/08/1999 | 0 - 1 | Middlesbrough | Premier League | |
| 4 | 23/08/1999 | 2 - 1 | Leeds United | Premier League | |
| 5 | 28/08/1999 | 2 - 0 | Arsenal | Premier League | |
| 6 | 11/09/1999 | 2 - 3 | Manchester United | Premier League | |
| 7 | 14/09/1999 | 5 - 1 | Hull City | League Cup 2nd round 1L | |
| 8 | 18/09/1999 | 2 - 2 | Leicester City | Premier League | |
| 9 | 21/09/1999 | 4 - 2 | Hull City | League Cup 2nd round 2L | |
| 10 | 27/09/1999 | 0 - 1 | Everton | Premier League | |
| 11 | 02/10/1999 | 0 - 0 | Aston Villa | Premier League | |
| 12 | 13/10/1999 | 1 - 2 | Southampton | League Cup 3rd round | |
| 13 | 16/10/1999 | 1 - 0 | Chelsea | Premier League | |
| 14 | 23/10/1999 | 1 - 1 | Southampton | Premier League | |
| 15 | 27/10/1999 | 1 - 0 | West Ham United | Premier League | |
| 16 | 01/11/1999 | 3 - 1 | Bradford City | Premier League | |
| 17 | 06/11/1999 | 2 - 0 | Derby County | Premier League | |
| 18 | 20/11/1999 | 2 - 0 | Sunderland | Premier League | |
| 19 | 27/11/1999 | 0 - 1 | West Ham United | Premier League | |
| 20 | 05/12/1999 | 4 - 1 | Sheffield Wednesday | Premier League | |
| 21 | 12/12/1999 | 2 - 0 | Huddersfield Town | FA Cup 3rd round | |
| 22 | 18/12/1999 | 2 - 0 | Coventry City | Premier League | |
| 23 | 26/12/1999 | 2 - 2 | Newcastle United | Premier League | |
| 24 | 28/12/1999 | 3 - 1 | Wimbledon | Premier League | |
| 25 | 03/01/2000 | 0 - 1 | Tottenham Hotspur | Premier League | |
| 26 | 10/01/2000 | 0 - 1 | Blackburn Rovers | FA Cup 4th round | |
| 27 | 15/01/2000 | 3 - 2 | Watford | Premier League | |
| 28 | 22/01/2000 | 0 - 0 | Middlesbrough | Premier League | |
| 29 | 05/02/2000 | 3 - 1 | Leeds United | Premier League | |
| 30 | 13/02/2000 | 1 - 0 | Arsenal | Premier League | |
| 31 | 04/03/2000 | 1 - 1 | Manchester United | Premier League | |
| 32 | 11/03/2000 | 1 - 1 | Sunderland | Premier League | |
| 33 | 15/03/2000 | 0 - 0 | Aston Villa | Premier League | |
| 34 | 18/03/2000 | 2 - 0 | Derby County | Premier League | |
| 35 | 25/03/2000 | 2 - 1 | Newcastle United | Premier League | |
| 36 | 01/04/2000 | 3 - 0 | Coventry City | Premier League | |
| 37 | 09/04/2000 | 2 - 0 | Tottenham Hotspur | Premier League | |
| 38 | 16/04/2000 | 2 - 1 | Wimbledon | Premier League | |
| 39 | 21/04/2000 | 0 - 0 | Everton | Premier League | |
| 40 | 29/04/2000 | 0 - 2 | Chelsea | Premier League | |
| 41 | 03/05/2000 | 0 - 2 | Leicester City | Premier League | |
| 42 | 07/05/2000 | 0 - 0 | Southampton | Premier League | |
| 43 | 14/05/2000 | 0 - 1 | Bradford City | Premier League |
| Name | League | FA Cup | League Cup | Total |
|---|---|---|---|---|
| Michael Owen | 11 | 0 | 1 | 12 |
| Titi Camara | 9 | 1 | 0 | 10 |
| Patrik Berger | 9 | 0 | 0 | 9 |
| Danny Murphy | 3 | 0 | 3 | 6 |
| David Thompson | 3 | 0 | 0 | 3 |
| Emile Heskey | 3 | 0 | 0 | 3 |
| Jamie Redknapp | 3 | 0 | 0 | 3 |
| Robbie Fowler | 3 | 0 | 0 | 3 |
| Sami Hyypia | 2 | 0 | 0 | 2 |
| Karl-Heinz Riedle | 0 | 0 | 2 | 2 |
| Erik Meijer | 0 | 0 | 2 | 2 |
| Layton Maxwell | 0 | 0 | 1 | 1 |
| Didi Hamann | 1 | 0 | 0 | 1 |
| Dominic Matteo | 0 | 1 | 0 | 1 |
| Steve Staunton | 0 | 0 | 1 | 1 |
| Steven Gerrard | 1 | 0 | 0 | 1 |
| Vegard Heggem | 1 | 0 | 0 | 1 |
| Vladimir Smicer | 1 | 0 | 0 | 1 |
| Own goals | 1 | 0 | 0 | 1 |
| Name | League | FA Cup | League Cup | Total |
|---|---|---|---|---|
| Vladimir Smicer | 4 | 1 | 2 | 7 |
| Dominic Matteo | 6 | 0 | 0 | 6 |
| David Thompson | 3 | 0 | 2 | 5 |
| Steve Staunton | 1 | 0 | 3 | 4 |
| Steven Gerrard | 3 | 0 | 0 | 3 |
| Michael Owen | 3 | 0 | 0 | 3 |
| Patrik Berger | 3 | 0 | 0 | 3 |
| Erik Meijer | 1 | 0 | 1 | 2 |
| Didi Hamann | 2 | 0 | 0 | 2 |
| Titi Camara | 1 | 1 | 0 | 2 |
| Danny Murphy | 2 | 0 | 0 | 2 |
| Sami Hyypia | 2 | 0 | 0 | 2 |
| Vegard Heggem | 0 | 0 | 1 | 1 |
| Emile Heskey | 1 | 0 | 0 | 1 |
| Jamie Redknapp | 1 | 0 | 0 | 1 |
| Jon Newby | 0 | 0 | 1 | 1 |
| Rigobert Song | 1 | 0 | 0 | 1 |
| Name | League | FA Cup | League Cup | Total |
|---|---|---|---|---|
| Sami Hyypia | 38 | 2 | 2 | 42 |
| Jamie Carragher | 36 | 2 | 2 | 40 |
| Sander Westerveld | 36 | 2 | 1 | 39 |
| Patrik Berger | 34 | 1 | 2 | 37 |
| Titi Camara | 33 | 2 | 2 | 37 |
| Dominic Matteo | 32 | 2 | 0 | 34 |
| Stephane Henchoz | 29 | 2 | 2 | 33 |
| Steven Gerrard | 29 | 2 | 0 | 31 |
| David Thompson | 27 | 1 | 3 | 31 |
| Michael Owen | 27 | 1 | 2 | 30 |
| Didi Hamann | 28 | 2 | 0 | 30 |
| Danny Murphy | 23 | 2 | 2 | 27 |
| Vegard Heggem | 22 | 0 | 3 | 25 |
| Vladimir Smicer | 21 | 2 | 2 | 25 |
| Erik Meijer | 21 | 0 | 3 | 24 |
| Jamie Redknapp | 22 | 0 | 1 | 23 |
| Rigobert Song | 18 | 1 | 2 | 21 |
| Steve Staunton | 12 | 1 | 3 | 16 |
| Robbie Fowler | 14 | 0 | 0 | 14 |
| Emile Heskey | 12 | 0 | 0 | 12 |
| Brad Friedel | 2 | 0 | 2 | 4 |
| Jon Newby | 1 | 2 | 1 | 4 |
| Karl-Heinz Riedle | 1 | 0 | 1 | 2 |
| Djimi Traoré | 0 | 0 | 2 | 2 |
| Layton Maxwell | 0 | 0 | 1 | 1 |
| Frode Kippe | 0 | 0 | 1 | 1 |
| Stig Inge Bjørnebye | 0 | 0 | 0 | 0 |
| Jørgen Nielsen | 0 | 0 | 0 | 0 |
| # | Player | Position |
|---|---|---|
| 1 | Sander Westerveld | Goalkeeper |
| 19 | Brad Friedel | Goalkeeper |
| 19 | Pegguy Arphexad | Goalkeeper |
| 26 | Jørgen Nielsen | Goalkeeper |
| 6 | Phil Babb | Defender |
| 23 | Jamie Carragher | Defender |
| 2 | Stephane Henchoz | Defender |
| 12 | Sami Hyypia | Defender |
| 30 | Djimi Traoré | Defender |
| 31 | Frode Kippe | Defender |
| 21 | Dominic Matteo | Defender |
| 4 | Rigobert Song | Defender |
| 5 | Steve Staunton | Defender |
| 29 | Stephen Wright | Defender |
| 20 | Stig Inge Bjørnebye | Defender |
| 14 | Vegard Heggem | Defender |
| 25 | David Thompson | Midfielder |
| 24 | Danny Murphy | Midfielder |
| 7 | Vladimir Smicer | Midfielder |
| 33 | Layton Maxwell | Midfielder |
| 28 | Steven Gerrard | Midfielder |
| 16 | Didi Hamann | Midfielder |
| 11 | Jamie Redknapp | Midfielder |
| 15 | Patrik Berger | Midfielder |
| 22 | Titi Camara | Forward |
| 32 | Jon Newby | Forward |
| 10 | Michael Owen | Forward |
| 18 | Erik Meijer | Forward |
| 9 | Robbie Fowler | Forward |
| 8 | Emile Heskey | Forward |
| 13 | Karl-Heinz Riedle | Forward |
| 27 | Haukur I. Gudnason | Forward |