Since his debut season, Benn has had to fight hard for a place in a Barbados team containing four West Indian international fast bowlers.

He beat off competition from Amit Jaggernauth for the spinner's spot and on 22 March 2008 made his debut for the West Indies in the first Test against Sri Lanka at Providence Stadium, Guyana.

In his first Test innings he scored 28 and helped contribute to some useful lower-order resistance after the West Indies top order had been dismissed cheaply.

On 6 December 2009, on the third day of the 2nd test against Australia, Benn managed his first five-wicket haul with career best figures of 5/155 after bowling 53 overs in the innings.

Despite Benn's efforts, his display was tarnished through a spitting incident with South African fast bowler Dale Steyn.