Career
Calaiò started his football career at Torino making his league debut against Reggina on 6 January 2000, he scored a goal for Torino three minutes into his debut. He made 20 league appearances in total for Torino. In January 2002 Calaiò was exchanged with Alessandro Cibocchi of Ternana with inflated price tag to create paper profit on both clubs (which Ternana was fined in 2010, 8 years later) and then a short spell with Messina followed.
In January 2003, was loaned by Pescara and turned permanently in June 2004.
He also returned to Torino Calcio in 2003 in exchange with Cibocchi again. In the third at Serie B, he scored 6 in the first half of the season.
Napoli Siena In July 2008, he joined fellow Serie A team, Siena in a co-ownership bid, for €2.3 million. in June 2009 Siena signed him outright for €1.25 million (which made Napoli register a financial loss of €105 million). He followed Siena relegated to Serie Bachelor in 2010 and finished as the runner-up and promoted back to top division.
On 10 June 2011 he signed a new 3-year contract.
Calaiò was one of the two starting strikers along with Mattia Destro in 2011-2012 Serie A season, scoring 11 goals in 25 league matches until he broken his leg in March 2012. Return to Napoli On 11 January 2013, his transfer to former team Napoli was officially announced. He arrived on-loan with the option to make the switch permanent if Napoli qualified for the Champions League during the 2013 season.
Catania On 11 July 2014, his transfer to Catania was officially announced.
He signed a two-year contract with an option for a third. International career He also received the Serie B U21 call-up for the match against Legnano.
He also call-up to 2000 Union of European Football Associations European Under-18 Football Championship qualification and played in qualifying match in 2001 edition Calaiò capped once for U17 team, at that time the feeder team of U18.
(now called Italy national under-18 football team) 2000-2001 Serie B (Torino).