DiBenedetto played for 10 seasons after being selected by the Boston Red Sox in the 37th round of the 2008 Major League Baseball draft. He spent his first three seasons with the Red Sox system before playing in Italy for Reggio Emilia in 2011. He then came back to affiliated baseball where he spent a season in the Baltimore Orioles system before returning to Europe, playing in Germany and Spain to finish his playing career.
 

The Fort Myers native has also worked in a number of other capacities in the game including as a coach, a scout, an analytics consultant, and a broadcast analyst. His coaching includes a stop at Georgetown as a volunteer for one season, as well as four years as a player/coach internationally.
 

DiBenedetto is a 2008 graduate of Trinity College in Hartford, Connecticut where he was a First Team All-New England Conference pick at shortstop as a senior. In addition, the Bantams went 45-1 during his final year en route to capturing the NCAA D-III National Championship. More recently, he earned his Masters in Sport Management from the University of Florida in 2017.