Di Francesco started his career with Tuscan teams Empoli and Lucchese. In 1995, he joined Piacenza, where he had the opportunity to play regularly in the top flight. In 1997, he was signed by A.S. Roma, winning an Italian championship title in 2001 with the "giallorossi". Following this triumph, he agreed to return to Piacenza, for 2 billion lire (€1.03 million by fixed exchange rate) and then retired in 2005 following stints with Ancona and Perugia.