Prior to join Ascoli, Di Biagio played for Lazio (1988-89), Monza (1989-92), Foggia (1992-95), AS Roma (1995-99), Internazionale (1999-2003), and Brescia Calcio (2003-2006). He was capped 31 times for Italy, scoring two goals. He played for his country in the 1998 and 2002 World Cups, as well as Euro 2000, when he did connect in a penalty shootout against the Netherlands. It was the first penalty he shot after the infamous miss during 1998 World Cup which eliminated Italy from the competition.
Di Biagio signed for Ascoli on November 2006, but the bid was not considered to be valid by the federation, since the player was not released for free by Brescia before the June 30 deadline. The bid was therefore postponed on January 2007, and in the meantime Di Biagio went on training with Ascoli, and played from November to December with Promozione club Polisportivo La Storta from Rome, coached by his friend and former Dundee F.C. and Lazio footballer Alessandro Romano. Di Biagio played his first Ascoli match on January 14, 2007, against Cagliari.
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