Club Early years Di Michele, whose mother is from
Casarano, began his career with
Lodigiani in the Italian
Serie C1 near to his hometown Guidonia Montecelio, and played for them from 1993 to 1996. He was then transferred to
Foggia Calcio in the Italian
Serie B. He had a short stint in Foggia, playing just two seasons before being transferred to
Salernitana. With Salernitana, he made his
Serie A debut, however the following year Salernitana were relegated to Serie B.
Udinese After two seasons with Salernitana in Serie B, he was transferred to
Udinese on an undisclosed fee for the 2001–02 season. After the 2001–02 season with Udinese, he played two seasons with Reggina, only to be transferred back to Udinese in 2004–05. In the 2005–06 season, he played half a season with Udinese and took part in the
UEFA Champions League. In a
2004–05 Coppa Italia match against
Lecce, he scored two goals, before replacing keeper
Samir Handanović in goal, after the latter was sent off. He stopped a key penalty in the final minutes of the game to ensure a 5–4 victory for Udinese.
Palermo Halfway through the 2005–06 season Di Michele's contract was sold to
Palermo for €5.35 million, with
Simone Pepe,
Salvatore Masiello and
Nicola Santoni moving to oppose direction in
co-ownership deals. He made his debut for Palermo in a Serie A home match against
Parma, in which he scored two goals in a 4–2 win. In his 2005–06 season, Di Michele played 19 matches, scoring seven goals. In March 2007, Di Michele was found guilty of illegal betting and received a three-month ban from Serie A. He also received a $27,000 fine. Betting was not illegal for Italian players until November 2005, but Di Michele, along with three others, placed bets through an illegal bookmaker. However, he was allowed to play in friendlies, and to take part in training, so he was able to retain match fitness.
Torino and West Ham United loan On 5 July 2007 Palermo announced they had sold him to
Torino, for €3.5 million He signed a four-year contract. On 31 July
FIGC announced Di Michele was suspended until November. He made 25 appearances with the
granata, scoring a total of six goals in the 2007–08 season. On 2 September 2008, Di Michele was loaned to
West Ham United, with an option for the English club to make the deal permanent. He made his debut for West Ham in the 3–2 defeat to
West Bromwich Albion on 13 September 2008, coming on as a substitute for the injured
Dean Ashton. In his second game for West Ham, on 20 September 2008, he scored his first goals in English football, and for West Ham, in the 3–1 home win against
Newcastle United However, at the end of the season manager
Gianfranco Zola did not take up the option of making the deal permanent. During 2009–10 season,
Ultras of Torino attacked the players during Di Michele's birthday party. After the incident the players involved: Di Michele,
Massimo Loviso,
Riccardo Colombo,
Aimo Diana,
Marco Pisano,
Francesco Pratali,
Paolo Zanetti were transferred to other clubs and only
Rolando Bianchi,
Matteo Rubin and
Angelo Ogbonna were remained.
Lecce Di Michele signed for
U.S. Lecce in January 2010. Having gained a place in the starting eleven, he was one of the decisive men in Lecce's successful Serie B campaign. In his first season back in Serie A with Lecce, he scored 8 goals in 23 appearances. On 24 June 2011, he renewed his contract for one more year. In the
2011–12 Serie A season, he led the team with 11 goals scored in league play. However, at the end of the season Lecce were relegated back to Serie B after a 17th-place finish.
Chievo On 13 July 2012, Di Michele moved to
A.C. ChievoVerona.
Later years In January 2013, Di Michele rescinded his contract with Chievo and was signed by his former club Reggina, eight years after leaving them. He joined the Serie B club to cover the loss of
Fabio Ceravolo, who transferred to Ternana for €500,000. In 2015, he left Reggina to join newly promoted
Lega Pro club
Lupa Roma.
International At international level, Di Michele made six appearances for the
Italy national football team between 2005 and 2006. He made his senior debut for Italy on 30 March 2005, at the age of 29, under coach
Marcello Lippi, in a 0–0 friendly home draw against
Iceland. He made his final appearance for Italy on 6 September 2006, under
Roberto Donadoni, in a 3–1 away loss to
France in a
European qualifier. ==Coaching career==