Liverpool acquired eight players in the transfer market, including Philipp Degen, Andrea Dossena and Diego Cavalieri who arrived in early July.

Liverpool began the season in good form; they won eight of their first ten matches before suffering a defeat against Tottenham.

Three successive draws at the turn of the year meant that Manchester United caught Liverpool and a 2–0 defeat by Middlesbrough at the end of February dented their hopes of winning the league.

Despite new signing Fernando Torres scoring 33 goals in all competitions, including 24 in the Premier League, the team finished in fourth place, 11 points behind eventual winners Manchester United.

[5][6] Goalkeeper Diego Cavalieri was signed from Brazilian club Palmeiras as backup to Pepe Reina,[7] while French striker David Ngog joined from Paris Saint-Germain.

[8] The biggest signing of the summer transfer window was the purchase of striker Robbie Keane from Tottenham Hotspur for a fee of £19.3 million.

[9] Midfielder Albert Riera joined from Spanish club Espanyol at the end of the summer transfer window.

[13] Later in July, striker Peter Crouch joined his former club, Portsmouth, for £11 million and goalkeeper Scott Carson was sold to West Bromwich Albion.

[14][15] Defender Steve Finnan and midfielder Danny Guthrie left in August to join Espanyol and Newcastle United respectively.

[20] Manchester United were the pre-season favourites to retain their league title with Chelsea considered their main challengers.

[21] The Guardian's Paul Doyle opined, "If they are to sustain a challenge for the title beyond Christmas, Liverpool will have to develop the offensive diversity and unpredictability to turn last season's costly draws against smaller teams into victories.

[26] The provisional fixture list was released on 16 June 2008, but was subject to change in the event of clashes with other competitions, international football, inclement weather, or matches being selected for television coverage.

In the sixth minute of stoppage time, Steven Gerrard scored from the edge of the penalty area to secure a 2–1 victory for Liverpool.

The win marked the first time, Liverpool manager Rafael Benítez had beaten United in the League since his arrival in 2004.

[34] Torres was confident Liverpool could challenge for the title following the victory: "We know if we can stay near the top of the table in January or February we can win it.

A Xabi Alonso goal in the 10th minute was enough to secure victory for Liverpool, as they won the match 1–0, becoming the first team since February 2004 to beat Chelsea at Stamford Bridge in the Premier League.

[40] Liverpool rebounded the following week as they beat West Bromwich Albion 3–0 at Anfield, courtesy of two goals from Keane and one from Álvaro Arbeloa.

[44] Liverpool travelled to Ewood Park to face Blackburn Rovers in their next match and returned to winning ways with a 3–1 victory.

Despite Arsenal striker Emmanuel Adebayor being sent off in the 62nd minute, Liverpool were unable to score a winning goal and the match finished 1–1.

Midfielder Lucas conceded a penalty for a foul on Jason Koumas, which was converted by striker Mido on his debut in the 83rd minute to level the score at 1–1.

Chelsea midfielder Frank Lampard was sent off in the 60th minute for a foul on Alonso, but Liverpool struggled to make their numerical advantage count.

Kuyt equalised with five minutes remaining before Torres scored 'a dramatic late header' to secure a 3–2 win for Liverpool.

[63] Following the resumption of club football after the international break, Liverpool travelled to Old Trafford to face league leaders Manchester United.

Like the FA Cup it is played on a knockout basis, with the exception of the second round and semi-finals, which are contested over a two-legged tie.

Damien Plessis pulled a goal back for Liverpool early in the second half, but three minutes later Pavlyuchenko scored again to extend Tottenham's lead.

[88] As Liverpool had finished fourth in the league the previous season, they needed to play a qualifying round against Standard Liège to ensure progression into the group stages.

Liverpool faced Marseille in the fifth match of the group stage and secured progression to the knockout phase, after winning 1–0 thanks to a Gerrard goal.

Drogba, defender Alex and midfielder Frank Lampard scored to give Chelsea a 3–2 and a three-goal advantage in the tie midway through the second half.

A further goal by Lampard in the 89th minute ended any hopes of a comeback as the match was drawn 4–4, with Chelsea winning the tie 7–5 on aggregate.

Lucas was the only player to be sent off during the season—he was shown a red card during Liverpool's replay of their fourth round FA Cup tie with Everton.