[2] In his debut season in the national league, he finished second in the scoring charts with 17 goals and assisted the club in securing the championship.
[3][4] He re-signed with Harbour View the following season and contributed a goal in the quarterfinal match of the 2007 CFU Club Championship tournament against Portmore United.
[6] In his third season with Harbour View, he appeared in the opening round of the 2008–09 CONCACAF Champions League where they were defeated by Club Universidad Nacional.
[27] In May 2014, Bryan left Vissai Ninh Bình for V.League 2 side Hanoi after the club was dissolved due to a match-fixing scandal.
[29] He received another attempt in early 2016 to return to the Vietnamese top tier after securing a trial run with Dong Thap.
[36] Bryan returned to the Canadian circuit the following season to play with Scarborough after York Region transferred several of their players to the eastern Toronto side.
[49] Bryan was named to the Jamaican Olympic Team by head coach Wendell Downswell to participate in the 2007 Lunar New Year Cup.
[52][53] Bryan was originally selected to represent the national team in the 2011 CONCACAF Gold Cup but withdrew after sustaining a leg injury while playing with Sông Lam Nghệ An.
[55] Bryan returned to the national program in a 2014 FIFA World Cup qualification match on 7 September 2012, against the United States.