The 1999–2000 season was the 109th season in Liverpool F.C.'s existence. The club finished fourth in the Premier League, thus qualifying for the 2000–01 UEFA Cup.

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

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.

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