Benjamin graduated from Saint Benedict"s College, a secondary school in Trinidad. He attended the University of Mobile, playing on the men’s soccer team from 1993 to 1996. In 1994, Benjamin and his teammates finished runner-up in the final of the National Association of Intercollegiate Athletics national men"s soccer championship.
In 1996, he was selected as an National Association of Intercollegiate Athletics All American. In April 1997, Benjamin signed with the New Orleans Riverboat Gamblers of the USISL A-League. In early 2000, Benjamin joined the Tennessee Rhythm, but was released in May.
In February 2001, the Charleston Battery signed Benjamin, but he played only one game before being released.
In 2002, he briefly played for the Hampton Roads Mariners. He finished his career with the New Orleans Shell Shockers of the USL Premier Development League.
Benjamin played for the Trinidad and Tobago national teams at both the youth and senior levels.
He was a member of the Trinidad and Tobago U-20 national team at the 1991 Fédération internationale de football association World Youth Championship.
