[2] After starting his youth career at York United in the St Thomas Parish leagues and Eastern Confederation Super League, Phillips made the move to Waterhouse Football Club, starting with their u21 team before becoming a senior team regular.

Phillips made only two appearances for Stoke, however, and in the summer of 2008 joined Oldham Athletic on trial with a view to a season-long loan.

Phillips was signed by USL Championship club Austin Bold FC early in their inaugural season, on 18 April 2019.

[10] Phillips has appeared for the Jamaica national football team a total of 72 times scoring twelve goals.

When I step onto the pitch before a game, I stop before the sidelines, taking to the ground with my hands, before I do the sign of the cross and look up at the sky.