Ramon Bailey

Ramon Bailey (born February 22, 1984) is a former Jamaican footballer who played as a midfielder.

Early career
Bailey played college soccer with Merced College where he was named to the All-American first team and received the MVP award. In 2005, he signed a contract with the MetroStars of the Major League Soccer. Bailey was confided to the team's reserve squad in his debut season. After a change in management, he was released by the club in 2006.

Finland
Following his release from New York, he secured a contract abroad in the Finnish Ykkönen with Kokkolan Palloveikot. Bailey would appear in the 2006 Finnish Cup final where Helsingin Jalkapalloklubi defeated Kokkolan.

Jamaica
In 2007, he returned to his native country to sign with defending champions Waterhouse F.C. in the Jamaica Premier League.

Canada
Bailey joined the interprovincial Canadian Soccer League in the summer of 2008 to play with Portugal FC. He re-signed with the Toronto-based club in 2009. In 2012, he signed with league rivals the Serbian White Eagles. He would help the Serbs secure a playoff berth by finishing sixth in the league's first division. In the opening round of the playoffs, the White Eagles defeated his former team Portugal FC (renamed SC Toronto). Their playoff journey would conclude in the next round after a defeat by Toronto Croatia.

Bailey returned to play with the Serbs for the 2013 season. He helped the team secure another playoff berth by finishing eighth in his sophomore year with Serbia. Kingston FC would eliminate Serbia in the opening round of the postseason. In 2014, he joined SC Waterloo Region. He helped Waterloo secure a playoff berth in his debut season. He recorded a goal against Toronto Croatia in the opening match of the playoffs. Bailey re-signed with Waterloo for the 2015 season. Waterloo would reach the championship finals where they lost the match to Toronto Croatia. In 2017, he contributed a goal against his former club the Serbian White Eagles in the preliminary round of the postseason.