Jamaica Bryan began his professional career in the
KSAFA Super League in 2005 with Rae Town. His stint with Rae Town lasted for three months as he was transferred to
Police Nationals during the winter transfer window. 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. 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. He also played in the final match of the Caribbean tournament where Harbour View defeated
Joe Public for the championship. 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. In April 2009, he played abroad in Norway's
1. divisjon on a loan deal to
Notodden FK. After a season in Scandinavia, he returned to the Jamaican top tier to resume play with Harbour View for the 2009-10 season. Throughout the season he helped the Kingston-based club secure another league title. He returned for his fifth season with the club the following year. Though he had a shortened season in Jamaica, he returned to finish the 2010-11 campaign once his loan deal ended around November 2011.
Vietnam His fifth season with Harbour View was shortened as he was loaned out abroad to the Vietnamese's
V.League 1 for
Sông Lam Nghệ An. The club went on to claim the league title. He also played in the
2011 AFC Cup where he recorded 3 goals in 3 appearances. In May 2011, Bryan broke his fibula while playing for Sông Lam Nghệ An. After failing to come to terms with Song Lam Nghe An he departed after the conclusion of the season. He returned to Vietnam for the 2012 season where he secured a deal with
Vicem Hai Phong. This tenure with Hai Phong only lasted a single season as he departed from the club the following year. Bryan would return to his former team Sông Lam Nghệ An in 2013. He would appear in 22 matches and record 8 goals throughout the season. During his stint with Vissai Ninh Binh, he had another run in the
Asian continental tournament. 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. After a five-year run in Asia, he returned to his former club Harbour View for the 2015-16 season. He received another attempt in early 2016 to return to the Vietnamese top tier after securing a trial run with
Dong Thap.
Canada In 2017, he played in the
Canadian Soccer League with
York Region Shooters. Bryan assisted the Vaughan-based team in securing a postseason berth by finishing third in the First Division. In the second round of the playoffs, he contributed a goal against the
Serbian White Eagles which advanced the club to the
CSL Championship. York Region would successfully win the championship title after defeating
Scarborough SC in a penalty shootout. 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. He helped Scarborough secure a playoff berth and scored a goal in the playoff semifinal match against
FC Ukraine United. He would participate in the championship final where Scarborough was defeated in a penalty shootout by
FC Vorkuta. Bryan returned to Scarborough for his sophomore season in 2019. He assisted the club in securing a postseason berth by finishing second in the top division. He would play in his third championship final where Scarborough would successfully defeat Ukraine United for the title. In 2020, he re-signed with Scarborough and assisted in securing the First Division title. He returned to sign with Scarborough for his fifth season in 2022. == International career ==