On 19 May 2008, Benjamin was released from Hereford United, being told his services will not be needed in the following season, despite being the club's third top goalscorer that season. He joined Conference North club Gainsborough Trinity on non-contract terms in August 2008, a week later after joining Gainsborough Trinity, the Lincolnshire Echo revealed the player had also been training with Cheltenham Town. Despite this Trevor was released by a 'disappointed' Steve Charles after just three appearances for Gainsborough Trinity, with the Blues noting that the Jamaican International had under performed in his games.