Born in Castellammare di Stabia, Cirillo started his career in the ranks of Reggina, and started enjoying regular first-team football after a 1996–97 switch to Serie C2 Tricase Calcio. In the summer of 1998, he returned to Reggina and helped them to promotion to Serie A. The following season was even better, with Cirillo scoring twice in 32 matches and catching the eye of F.C. Internazionale Milano, joining in 2000. He appeared 24 times in his sole season in Milan before moving to U.S. Lecce for 6,000 million lire in co-ownership deal along with Giorgio Frezzolini for 2,500 million lire in co-ownership deal (swapped with Erminio Rullo of Lecce for 3,000 million lire in co-ownership deal and 5,500 million lire cash). In June 2002 Lecce acquired Cirillo (€306,000), Frezzolini (free) and Rullo (€151,000) outright.

12 months later he switched again, this time to AEK Athens F.C., and proved influential for the Greek runners-up spot in 2006 and 2007. He was a big fan favorite in Athens for his passion, and was under contract until 2008. However, on 29 April 2007 Cirillo played his last match with AEK against Skoda Xanthi F.C. in the Greek Super League. Right after the game, for which Cirillo was given the Man of the Match award, the much-spread rumours that he was leaving the club at the end of the season were confirmed.

On 4 July 2007, Cirillo signed a two-year deal for Spanish outfit Levante UD. In January 2008, due to Levante’s inability to pay agreed wages he, alongside countryman Marco Storari left the club, with Cirillo signing for Reggina, the club where he grew as a player. Cirillo mutually terminated his contract with Reggina in June 2009, and later that month PAOK FC signed him until June 2011 on free transfer.

On 28 January 2013, Cirillo signed a six-month deal for French club FC Metz, with the option of a further year. This option was not taken, and on 26 August 2013, Cirillo signed a one-year private agreement for AEK Athens, returning to the club after six years away.

On 21 August 2014, Cirillo was the first pick in the Indian Super League Inaugural International Draft, signed by FC Pune City.

In 2015, he returned to Reggina, the club in which he started his career to finish his career there. He retired in 2015 and now he plans on becoming a manager in the future.