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.

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.

[7] 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.

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.

Liverpool's attack was bolstered with the club record £11 million signing of Leicester City's Emile Heskey on 10 March 2000.

A goalless draw against Southampton followed, and on the final day of the season, 14 May, the Reds travelled to a Bradford City side battling it out with Wimbledon to avoid the last relegation place.

The result also relegated Wimbledon, who, 12 years to the day, had beaten the Reds in one of the greatest FA Cup final shocks of all time.