Born in
Trieste, Milanese started his senior career at
Serie D side
Monfalcone. He then played for
Serie C1 side
Massese, making 22 appearances before to join hometown club
Triestina, where he played 50 Serie C1 matches in two seasons. In summer 1994 he was signed by Serie A side
Cremonese, giving him the chance to make his top flight debut. He then played for
Torino and
Napoli, again at Serie A level. In summer 1997, he was signed by
Parma, but in mid-season he was loaned to
Inter Milan. He played his first match for Inter on 25 January 1998, as a substitute for
Youri Djorkaeff in a 1–1 draw to
Empoli; he also remained at Inter the following season. In summer 1999, he joined
Perugia in
co-ownership deal. In summer 2003, he left for Serie A newcomers
Ancona but suffered his second relegation (the first being while at Torino). He then re-joined Serie B side Perugia. In August 2005, he joined
Queens Park Rangers in one-year deal. Which he changed to play as a centre defender. He played 26 league matches but missed a month in September. His contract was later extended and released in May 2007. In August 2007 he was signed by
Salernitana and won Serie C1 champion. He then left for
Lega Pro Seconda Divisione side
Varese Milanese planned to retire in July 2009 and aimed to qualify as a FIFA licensed football agent. ==Post-playing career==