Following a series of strong performances in the 2007/08 Carib Beer Cup, Benn was called up to the West Indies Test squad. He beat off competition from Amit Jaggernauth for the spinner's spot and on 22 March 2008 he made his debut for the West Indies in the first Test against Sri Lanka at Providence Stadium, Guyana. He bowled quite well in Sri Lanka's first innings, bowling 40 overs at an economy of 3.00, but went unrewarded. 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. In Sri Lanka's second innings, he claimed his first Test wicket, Mahela Jayawardene (caught by Shivnarine Chanderpaul), and finished with 3/59. He could only manage 7 with the bat in his second innings as the West Indies slid to defeat by 121 runs.