The 1999–2000 season was Liverpool Football Club's 108th season in existence and their 38th consecutive season in the top-flight of English football. The club finished fourth in the Premier League, thus qualifying for the 2000–01 UEFA Cup.
Players
First-team squad
Squad at end of season
Left club during season
Reserve squad
Transfers
In
Sami Hyypiä - Willem II, 18 May, £2,600,000
Titi Camara - Marseille, 2 June, £2,600,000
Stéphane Henchoz - Blackburn Rovers, 3 June, £3,500,000
Sander Westerveld - Vitesse, 15 June, £4,000,000
Vladimír Šmicer - Lens,1 July, £4,200,000
Erik Meijer - Bayer Leverkusen, 1 July, Free
Dietmar Hamann - Newcastle United, 22 July, £8,000,000
Emile Heskey - Leicester City, 10 March, £11,000,000
Out
David James - Aston Villa, 23 June, £1,800,000
Steve McManaman - Real Madrid, 1 July, free
Jean-Michel Ferri - Sochaux, 14 July, £1,500,000
Tony Warner - Millwall, 17 July, free
Jamie Cassidy - Cambridge United, 22 July, free
Sean Dundee - Stuttgart, 30 July, £1,000,000
Paul Ince - Middlesbrough, 30 July, £1,000,000
Øyvind Leonhardsen - Tottenham Hotspur, 6 August, £3,000,000
Bjørn Tore Kvarme - Saint-Étienne, 30 August, £1,000,000
Karl-Heinz Riedle - Fulham, 28 September, £200,000
Ian Dunbavin - Shrewsbury Town, 22 January, free
Eifion Jones - Blackpool, 23 March, free
Rob Jones - West Ham United, free, 24 July
Events of the season
After a disappointing seventh-place finish the previous season, which left Liverpool without even UEFA Cup qualification, manager Gérard Houllier began to rebuild his squad and made seven close season signings. The attack was bolstered with the arrival of Titi Camara, Erik Meijer and Vladimír Šmicer. Succeeding Aston Villa-bound David James in goal was Dutchman Sander Westerveld. A new look central defence featured Stéphane Henchoz and Sami Hyypiä. Following the summer departure of former captain Paul Ince, Jamie Redknapp was made the new captain of the side, with Robbie Fowler appointed as vice-captain.
The season began on 7 August 1999 with a 2–1 win at Sheffield Wednesday, with Robbie Fowler and the debutant Titi Camara finding the net. However, the next game saw newly promoted Watford – in the top flight for the first time in over a decade – travel to Anfield and come away surprise 1–0 winners. Defeat followed in the next game as Liverpool travelled to Middlesbrough, but then came victories over Leeds United and Arsenal which saw the Reds occupy eighth place as the first month of the season drew to a close.
September saw the Reds navigate the second round of the Football League Cup with a comfortable aggregate win over financially troubled Division Three side Hull City, though they failed to achieve any victories in the league, losing 3–2 at home to Manchester United (with Jamie Carragher scoring two own goals), drawing 2–2 at Leicester City and finally losing 1–0 at home to Everton in the Merseyside derby. This left Liverpool 12th by the end of September, while their cross-city rivals were showing signs of a revival after three dismal seasons by occupying sixth place. Things improved slightly in October with two league victories over Chelsea and West Ham United. Southampton had ended Liverpool's League Cup hopes with a third round defeat earlier in the month, which ended with Liverpool's league standing slightly improved to ninth place. With a third of the season now gone, they were eight points off the top of a table being led by Leeds United.
November was a much better month for the Reds, who achieved wins over Bradford, Derby County and Sunderland to occupy fifth place by 20 November. They were now just six points behind leaders Manchester United. However, the month ended on a low note as they lost 1–0 at West Ham United.
Liverpool's revival continued in December as they beat struggling Sheffield Wednesday 4–1 at Anfield. With the FA Cup third round unusually being played before Christmas, they travelled to Division One promotion chasers Huddersfield Town on 12 December and came away 2-0 victors. A 2–0 win over Coventry City on 18 December meant that the Reds were still fifth in the league at Christmas, six points behind Manchester United.
Their FA Cup quest ended in a shock 1–0 fourth round defeat at home to Blackburn Rovers.
Liverpool's attack was bolstered with the club record £11 million signing of Leicester City's Emile Heskey on 10 March 2000.