Bennett was born in Valdosta, Georgia. He attended Valdosta High School, and played quarterback for the Valdosta Wildcats high school football team. As a junior in 1960, he led the Wildcats to a 20–14 victory over Avondale High School in the Georgia state championship game. Bennett ran for a touchdown, threw for another, and ran for a third with twenty-nine seconds remaining to win the game. As a senior in 1961, he was recognized as a high school All-American.
College career
Bennett accepted an athletic scholarship to attend the University of Florida in Gainesville, Florida, and played for coach Ray Graves' Florida Gators football team from 1963 to 1965. Bennett set a Gators career record with thirteen interceptions, including three in the Gators' 21–14 victory over the Georgia Bulldogs in 1963. He was the senior defensive team captain of the 1965 Gators team that finished 7–3 and earned a berth in the 1966 Sugar Bowl, the Gators' first-ever New Year's Day bowl. He was a first-team All-Southeastern Conference selection in 1964 and 1965, and a United Press International first-team All-American in 1965. Ray Graves rated Bennett as the Gators' best free safety of the 1960s. Bennett graduated from the university with a bachelor's degree in 1968, and was later inducted into the University of Florida Athletic Hall of Fame as a "Gator Great." In a 2006 article series published by The Gainesville Sun, the Sun sports editors rated him as the No. 38 all-time greatest Gator from the first 100 years of Florida football.
Professional career
Bennett joined the CFL's Saskatchewan Roughriders in 1966, and participated in the team's 29–10 Grey Cup victory over Ottawa. He played for the Roughriders from to, and became one of the league's top safeties. He also was the team's go-to "good hands" player for onside kicks, and served as the team's emergency quarterback, completing 8 of 17 passes in his CFL career. He registered career highs of eight interceptions in both and. In seven CFL seasons, Bennett played in 112 games, and totaled thirty-five interceptions, and 606 return yards. His career interception total still ranks third on the Roughriders' all-time list. Bennett's teammates selected him as the team captain four times, and he earned six Western Conference All-Star selections and one CFL All-Star selection.
