A left-handed opening batsman, Omar Phillips was among seven Test debutants in the St Vincent Test against Bangladesh in 2009 when the seniors went on strike over contracts. He made an impression in his first match for West Indies, falling six short of a debut century in St Vincent.

Phillips played just one game for Combined Campuses and Colleges in his first season (2007-08) but was a regular the next. He was the second-highest run-getter for CCC with 601 runs in nine games and cracked 204 against Leewards Islands in Nevis, also his maiden first-class century.