In July 2008, Calaiò joined fellow Serie A team, Siena in a co-ownership bid, for €2.3 million.

[7] He was one of the two starting strikers along with Mattia Destro in 2011–12 Serie A season, scoring 11 goals in 25 league matches until he broke his leg in March 2012.

He arrived on-loan with the option to make the switch permanent if Napoli qualified for the Champions League during the 2013 season.

[16] Calaiò capped for both Italy U21 and Serie B U21 selection which played the latter for the match 3–2 won Belgium U21 on 30 March 2004.

[19] He also call-up to 2000 UEFA European Under-18 Football Championship qualification and played in qualifying match in 2001 edition.

(now called Italy national under-18 football team) A left–footed striker, Calaiò was mainly known for his heading, ability in the air, and eye for goal; he was also an accurate penalty taker.