Addlery attended high school at Jamaica College, and played in the Manning Cup. He played for Cooreville Gardens in the Syd Bartlett League, Real Mona-U20 in the Major League, and Alvernia Prep. While earning his bachelor's degree in Business Administration at Division IICalifornia University of Pennsylvania from 1999–2002, Addlery was a two-time NSCAA/Umbro All-Region selection. He was a four-time first-team PSAC all-star and PSAC Rookie of the Year in 1999. In 75 career games, he scored 54 goals and recorded 20 assists for the Vulcans. He ranks second on the Cal U career goals and points lists and fifth in career assists.
Professional
After college, Addlery turned pro as the first Jamaican in the T&T Professional Football League, playing for Starworld Strikers in 2003 and CL Financial San Juan Jabloteh in 2005. In 2006, he played football as the first Jamaican in Vietnam for SHB Đà Nẵng F.C.. He had signed with the Virginia Beach Mariners for the 2007 season, but within the month the franchise, caught in the midst of an ownership squabble, was terminated by the United Soccer Leagues. After a trial, he was signed by D.C. United in April 2007, scoring his first MLS goal on 28 June, a game winner against the Colorado Rapids at RFK Stadium. On 12 October 2008 he helped the Whitecaps capture their second USL First Division Championship beating the Puerto Rico Islanders 2–1 in Vancouver. On 5 November 2008 he was released along with teammate Omar Jarun. In January 2009, Addlery traveled to Puerto Rico to join the Puerto Rico Islanders of the USL-1 at their training camp on trial, signing with the club on 18 February. He had an immediate impact, scoring in both games of the Quarterfinals series against C.D. Marathón in the CONCACAF Champions League. The goals helped his club towards the semifinals in that competition. He also scored one of the two goals against C.D.S.C. Cruz Azul of Mexico in the 2-0 Islanders win in the first leg of the semifinal.Addlery finished the 2009 season with 15 goals in all competitions for the Islanders. In November 2009, he signed on loan for Salvadoran side Águila of the Salvadoran Primera División, and scored 5 goals during his stint with the club. In 2010, after spending a few weeks training with Cruz Azul in Mexico, Addlery returned to the Islanders where he is expected to lead the attacking frontline. Addlery scored 2 goals in three matches as he led the Islanders to the 2010 Caribbean Club Championship in Trinidad and Tobago. Although Addlery has continued scoring goals, Puerto Rico Islanders have struggled midway through USSF D2 season. In July 2010 Addlery scored 2 goals, leading the Puerto Islanders in a 4–1 defeat of then MLS league leaders, LA Galaxy which paved the way for their progression to the group stages of the CONCACAF Champions League for the third consecutive year. Addlery continued his scoring form and has scored three goals in three games in the CONCACAF Champions League. Addlery finished 2010 with 15 goals again in all competitions leading Puerto Rico to the USSF Division 2 Pro League title. In February 2011, Addlery resigned with the Puerto Rico Islanders in the NASL and was also named team captain. He is the All-Time Leading Goal Scorer in PR Islanders FC history. In January 2013, Addlery signed with the Carolina Railhawks.
Prior to the 2018 Premier Development League Season, Addlery was hired by Georgia-based club Peachtree City MOBA to be an assistant with the senior team under his former Whitecaps teammate Omar Jarun.
