At the age of 28, Benjamin dropped out of the professional game and firstly signed for Conference North side Gainsborough Trinity.

In 2010, he briefly joined Australian semi-pro side Sunshine George Cross, but failed to make an appearance and returned to the English Non-league game where he went on to feature for Bedlington Terriers, Wroxham and Morpeth Town.

He then signed as a trainee for Cambridge United where he made his professional début as a 16-year-old, against Gillingham in a 0–0 draw, during his time there he scored 46 goals in 146 appearances.

[3] Following some impressive displays for Cambridge United, Benjamin signed for Leicester City (where his work rate and goal celebrations saw him become something of a cult figure).

He was signed for a fee of £1.3 million by manager Peter Taylor, who snapped up Benjamin as a replacement for the departed Emile Heskey who had joined Liverpool.

[14] At Brighton he scored five goals in ten league appearances and manager Mark McGhee was keen to extend his loan to the end of the season.

[17] In the summer of 2005 Benjamin was released again and later signed for Peterborough United on a three-year deal, stating his main motivation was to gain first team football.

He continued his impressive form in the first half of the season and became something of a fans favourite at Edgar Street, scoring his share of goals.

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.

Benjamin had trials with Cheltenham Town, Gillingham and AFC Bournemouth at the start of the 2008–09 season, but failed to earn a contract at any of the three clubs.

[31] However, Benjamin moved on to Kidsgrove Athletic in the Northern Premier League Division One South, making his debut in a 5–2 win against Brigg Town on 14 February 2009.

On 7 August 2009, Trevor Benjamin signed for Conference National newcomers Tamworth, following a successful trial period with the club.

[33] He made his debut the following day in a Conference National away fixture against Stevenage Borough, Benjamin came on as a 79th-minute substitute for midfielder Tom Shaw.

[34] He moved on to Harrogate Town in the Conference North, making his debut and scoring two goals in a 3–2 loss against Northwich Victoria on 3 October 2009.