He 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 along with Giorgio Frezzolini (swapped with Erminio Rullo of Lecce and cash). Cirillo then returned to Reggina in 2002–03, rejoined Lecce and was loaned to A.C. Siena in quick succession.
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.