The highly-experienced striker signed for West Ham United initially on loan for one year with a view to a possible permanent transfer. He was handed the No32 shirt, the number worn previously by Carlos Tevez and Kieron Dyer.
He began his career with spells at Lodigiani, Foggia and Salernitana, where 40 goals in 92 appearances at the latter convinced Serie A side Udinese to secure his services in 2001. He played 25 times for them in his first season before moving on to enjoy a two-year spell at Reggina where he made 62 appearances.
In 2004, he moved back to Udinese where he scored 18 goals in 53 games and gained valuable Champions League experience. One of Di Michele's most memorable moments for Udinese was in a Coppa Italia match against Lecce. Having already scored two goals, he took over the goalkeeping duties after his side's No1 was sent off and saved a last-minute penalty to help his team to a 5-4 victory.
In 2006, he was transferred to Palermo where he instantly marked his arrival by scoring two goals on his debut against Parma. He played a total of 48 games for the Sicilian club scoring 16 goals, including one in a UEFA Cup first-round tie against West Ham United.
The summer of 2007 saw Di Michele join Torino where he scored six times in 24 appearances for the Turin-based club. He was much in demand by the time the 2008/09 season rolled around but it was West Ham United who managed to secure his services and he was delighted to sign on at the Boleyn Ground.