Dossena started his professional career at Verona in 2001, having progressed through the club's youth ranks. Having made 99 league appearances for Verona, he joined Treviso in 2005, and made 21 league appearances for the club. He then joined Udinese in 2006, and had a successful two-year spell, which, after making 63 league appearances, saw him switch to English side Liverpool in July 2008. However, he struggled to adapt to the English game, making just 18 league appearances in two seasons, and he returned to Italy in January 2010, when he signed for Napoli. Although he quickly established himself in the team, he fell out of favour during the 2012–13 season, and was loaned to Palermo, where he made 11 league appearances. In September 2013, having made 83 league appearances for Napoli, Dossena returned to England when he joined current club Sunderland.