A right-arm off-spinner by trade, Shillingford was brought on to the West Indies side after an impressive first-class record. Gradually he shaped up to be a potent threat in the West Indies test bowling line-up. He came into the limelight picking 11 wickets in the second test of Australia’s tour to West Indies in 2012. It was the first time in nearly 50 years that a West Indian spinner was picking over 10 wickets in a Test. Follow that in the West Indies tour to India in 2013, he spearheaded an otherwise weak attack and ended up as the joint second top-wicket-taker in the series. In the Caribbean Premier League, he was drafted by the St Lucia franchise in their year of inception in 2013, and has played all their seasons till 2016.