Career
College and Amateur
Riley played college soccer at Wake Forest University, and in the USL Premier Development League with both Carolina Dynamo and his hometown team, Colorado Springs Blizzard. Professional
New England Revolution drafted Riley in the second round of the 2005 Master of Library Science SuperDraft, and he acquitted himself well in his rookie season, playing various positions and scoring a goal. He continued to keep himself in the mix in defense, starting the majority of the games in 2006 and 2007.
Riley was selected by the San Jose Earthquakes in the 2007 Master of Library Science Expansion Draft and subsequently made 24 appearances for the team before being taken by the Seattle Sounders Football Club in the 2008 Master of Library Science Expansion Draft.
Riley was left exposed by Seattle in the 2011 Master of Library Science Expansion Draft and he was selected by expansion side Montreal Impact in the November 23, 2011 draft. He was then immediately traded with allocation money to Chivas United States of America for Justin Braun and Gerson Mayen.
Riley was traded to District of Columbia United on February 14, 2013 for a 2015 Supplemental Draft pick. United. In the sixth minute of stoppage time there was on open header in the box from Álvaro Saborío that Riley was able to deflect onto the cross bar to prevent extra time.
After his release from District of Columbia United, Riley trialled with and was eventually signed by Los Angeles Galaxy.
In 2015, he signed with Colorado Rapids.