Raif, the son of the coach Mel Gwinnett was attached to Exeter City from 2003, when he was with the Under-13's development squad. Working up through the age groups, Raif was with the U-16's development squad at the Centre of Excellence in 2006/07.

He joined Torquay in 2008 and moved to Weymouth in 2009, he also played at Truro City, Paulton Rovers, Bideford, Bath City, and Taunton Town.