[1] While earning his bachelor's degree in Business Administration at Division II California University of Pennsylvania from 1999 to 2002, Addlery was a two-time NSCAA/Umbro All-Region selection (2000 and 2002).

[3] After college, Addlery turned pro as the inaugural Jamaican in the T&T Professional Football League, playing for Starworld Strikers in 2003[4] and CL Financial San Juan Jabloteh in 2005.

He had signed with the Virginia Beach Mariners for the 2007 season,[6] but within the month the franchise, caught in the midst of an ownership squabble, was terminated by the United Soccer Leagues.

[7] After a trial, he was signed by D.C. United in April 2007,[5] scoring his first MLS goal on 28 June, a game winner against the Colorado Rapids at RFK Stadium.

[16] He made his first international appearance as a member of Jamaica national U-20 team in the qualifying matches for the 2001 FIFA World Youth Championship in Argentina.

Addlery then received his first Jamaica senior national team call under John Barnes in May 2009 and eventually was named to the 2009 Gold Cup squad.

He featured in matches against Haiti, Peru, El Salvador and Costa Rica[6] 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.