Dean Bennett has an extensive baseball background. His playing days started young and continued through Little League, High School, American Legion, and his Division 1 collegiate baseball at University of Massachusetts, Amherst, where he was a four-year starter and captained the team both his junior and senior years. He lead the team in stolen bases, runs, and fielding percentage. He was selected to the All Yankee Conference Team as a Freshman and Sophomore. He played one very successful season in the Boston Park League when he and many of his UMass teammates became champions of the much heralded Park League. He continues to play today in the Metro-West Over-30 Baseball League for the Framingham Orioles who won their fifth consecutive League Championship in 2005.

He is (currently inactive due to his RBI's activities) a certified member of the Massachusetts Baseball Umpires Association (MBUA).

Coach Bennett has served as the President of the Northbridge Little League and currently coaches the grade 7 and 8 baseball team at Northbridge Middle School where he is also a full-time Language Arts teacher for grade 8.

In 1982, he completed his college internship in Public Relations with the Boston Red Sox at Fenway Park.