In 1994, Benjamin and his teammates finished runner-up in the final of the NAIA national men's soccer championship.
[3] In February 2001, the Charleston Battery signed Benjamin, but he played only one game before being released.
He finished his career with the New Orleans Shell Shockers of the USL Premier Development League.
[5] 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 FIFA World Youth Championship.