Sassano was drafted with the 32nd pick of the 2008 MLS SuperDraft by New York Red Bulls and made his debut on 5 April 2008 in a home game against Columbus Crew.

Following the 2009 Major League Soccer season, Sassano went on a three-week training stint with sister club FC Red Bull Salzburg.

[2] On December 15, 2010, Sassano was selected by Los Angeles Galaxy in Stage 2 of the Re-Entry draft[3] and subsequently traded to Sporting Kansas City.

[10] After multiple injuries, including two knee surgeries in 2012, Sassano chose to retire as a professional soccer player, but he wished to remain involved in the sport.

[12] On March 14, 2018, Sassano was named the technical director of FC Cincinnati during their final season in the United Soccer League.