On 4 July 2008, Liverpool confirmed the signing of Dossena on a four-year deal for an undisclosed fee, reported to be in the region of £7 million, becoming the second Italian to play for the club, behind Daniele Padelli.

Dossena was signed as a direct replacement for John Arne Riise who left for Roma.
On 10 July 2008, it was announced that Dossena would wear the number 2 shirt.

His debut for Liverpool came on 16 August in the 1–0 Premier League win over Sunderland at the Stadium of Light.
The start to his career at Liverpool was marked by poor form and he was unsatisfied with his performances, telling The Guardian:
"I am not fully happy with my level.
I must now get to a high level and maintain that, but first I have to battle to win selection.
I am learning all the time".

 Dossena reinforced that he was committed to the club and explained that he was having difficulties adjusting because the pace of English football was significantly different from what he had experienced in Serie A. Despite his largely unimpressive performances, he received more opportunities to prove himself in the first team as Fábio Aurélio, Liverpool's favoured left back, suffered an injury in late November.
He lost his first team slot with Aurelio's return from injury combined with the emergence of Emiliano Insúa.
He scored his first goal for Liverpool on 10 March 2009 against Real Madrid in the UEFA Champions League after coming on as a substitute.
He scored his first goal in the Premier League four days later, on 14 March in the 4–1 victory against Manchester United at Old Trafford.
He scored both goals playing as an auxiliary left-winger as a late substitute in both games.
On 4 July 2008, Liverpool confirmed the signing of Dossena on a four-year deal for an undisclosed fee, reported to be in the region of £7 million, becoming the second Italian to play for the club, behind Daniele Padelli.
Dossena was signed as a direct replacement for John Arne Riise who left for Roma. On 10 July 2008, it was announced that Dossena would wear the number 2 shirt.
His debut for Liverpool came on 16 August in the 1–0 Premier League win over Sunderland at the Stadium of Light. The start to his career at Liverpool was marked by poor form and he was unsatisfied with his performances, telling The Guardian:
"I am not fully happy with my level. I must now get to a high level and maintain that, but first I have to battle to win selection. I am learning all the time".
 Dossena reinforced that he was committed to the club and explained that he was having difficulties adjusting because the pace of English football was significantly different from what he had experienced in Serie A. Despite his largely unimpressive performances, he received more opportunities to prove himself in the first team as Fábio Aurélio, Liverpool's favoured left back, suffered an injury in late November. He lost his first team slot with Aurelio's return from injury combined with the emergence of Emiliano Insúa. He scored his first goal for Liverpool on 10 March 2009 against Real Madrid in the UEFA Champions League after coming on as a substitute. He scored his first goal in the Premier League four days later, on 14 March in the 4–1 victory against Manchester United at Old Trafford. He scored both goals playing as an auxiliary left-winger as a late substitute in both games.
Andrea Dossena