He spent six years playing with Sporting Central Academy in the Jamaica National Premier League, eventually becoming the club's captain.

Watson had trials in England and Denmark, but after training with the club during the 2011 pre-season, Watson signed with Houston Dynamo of Major League Soccer on 15 April;[4] he made his Dynamo debut on 23 April 2011 in a 1–1 tie with Chicago Fire.

Watson was traded to FC Dallas on 19 February 2013 in exchange for a second-round 2015 MLS SuperDraft pick.

[7] On 4 March 2016, it was announced that Watson had resigned with Dallas and then been traded to New England Revolution for a third-round pick in the 2017 MLS SuperDraft.

[12] Watson made his international debut for the Jamaica national team on 26 July 2008 in a friendly against El Salvador and has since gone on to make 13 appearances for the Reggae Boyz.