Di Napoli started his career in minor Italian clubs, before being picked up by Napoli when Freddy Rincón's loan deal expired. Di Napoli scored five times for the Neapolitans, before being sold to Internazionale, where he was unable to make an impact. In 1998, he was signed by Empoli on loan. In June 1999, he was signed by Piacenza for 7 billion Italian lire. In January 2005, his contract with Messina was extended to summer 2008.
After Messina went bankrupt, Siena signed him on free transfer and loaned him to Salernitana. He guided the Campanian side to promotion in the Italian Serie B, and was acquired half of the registration rights in July 2008. In his Serie B season with Salernitana, he provided 13 goals, being instrumental into guiding his side into their relegation escape. In September 2009, he left Salernitana by mutual consent in order to return to Messina, joining the giallorossi, now in Serie D, on a free transfer with the aim to guide them back into professionalism.
The forward joined in summer 2010 from Italian Serie D football team Messina to Venezia. He played in the first half of the season 11 games and scored two goals for Venezia before joined on 2 December 2010 to Caronnese.
Coaching career
After his retirement, Di Napoli took his first full coaching role in July 2012 at amateurs Rieti of Eccellenza Lazio, then resigning later in November 2012 due to personal reasons. In August 2013 he took the reins of Serie D club Riccione, resigning in December 2013 due to financial issues. On 26 July 2014 he was named new head coach of Lega Pro club Savona. Di Napoli undertook his first move abroad in late 2014, when on January 31, 2014, he signed for Maltese club Vittoriosa Stars, in view of the 2015 remaining season. He was successively named head coach of Serie D club Messina in August 2015, but was forced to quit in February 2016 after being disqualified for four years due to his involvement in the 2015 Italian football scandal. His sentence was then reduced to 3 years and 6 months on appeal. In December 2017, he was acquitted from all charges on the related criminal trial. His disqualification ended officially on 12 July 2019, on which day he announced he was in talks to become head coach of Eccellenza amateurs Cologno.
