Benjamin graduated from Saint Benedict's College, a secondary school in Trinidad.
In 1994, Benjamin and his teammates finished runner-up in the final of the NAIA national men's soccer championship.
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.