Ventola played for several clubs in Italy throughout his career, and also had a loan spell with English side Crystal Palace.

At international level, he was a member of the Italian under-23 squad at the 2000 Summer Olympics in Sydney; he received his only senior call-up for Italy in 1998, although he did not come off the bench.

[2][6] Ventola signed for Inter Milan during the 1998–99 season, making 21 appearances in the league, and scoring six goals, playing alongside other notable forwards, such as Ronaldo, Roberto Baggio, Iván Zamorano, Andrea Pirlo, and Youri Djorkaeff, albeit mainly as a substitute.

[2] Premier League side Crystal Palace signed him on transfer deadline day in August 2004 on a season-long loan, but this was wrecked by injury and he only made a handful of appearances.

In his first season back at the club, he helped his team to win the 2005–06 Serie B title with his decisive goalscoring performances,[4] scoring 15 goals in 35 appearances.

On 25 April, he scored a brace in a 3–3 draw against Cremonese, which allowed Novara to win promotion to Serie B.

[4] Ventola played his first competitive international match for the Italy national under-17 football team (made up of players born in and after 1977), in a 1994 UEFA European Under-16 Championship qualifying fixture; in total, he scored one goal in two appearances for the under-17 side, featuring as a substitute for Ivano Montanaro, and as a starter respectively.

He made his debut for the Italy under-21 side on 3 October 1996, at the age of 18, in a 1998 UEFA European Under-21 Championship qualifying match, coming on as a substitute for Fabrizio Cammarata.

[2][17][21] An agile and talented right-footed player, with good technique, Ventola was considered one of Bari's and Italy's most promising prospects in his youth, although he suffered many injuries throughout his career.