He is famed for being a prime example of a journeyman footballer, having represented 29 teams in his career, and making over 350 appearances in the Football League between 1995 and 2008. He also holds the record for the most league clubs played for, which is 16. He most notably spent time in the Premier League with Leicester City, who he joined in 2000 from Cambridge United. He was capped by England U21 but went on to feature for Jamaica as a full international, where he earned two caps. Benjamin has also played as a professional in the Football League for Crystal Palace, Norwich City, West Bromwich Albion, Gillingham, Rushden & Diamonds, Brighton & Hove Albion, Northampton Town, Coventry City, Peterborough United, Watford, Swindon Town, Boston United, Walsall and Hereford United.