Phelan grew up in Enfield, Connecticut, and attended Wilbraham & Monson Academy, where he was named the 2003 Gatorade National High School Player of the Year.
Phelan was drafted in the first round (10th overall) of the 2008 MLS SuperDraft by Toronto FC but did not make a first team start before being traded to New England Revolution on June 4, 2008.
[citation needed] After one season in Finland, Phelan returned to the United States when he signed for NASL club San Antonio Scorpions on March 1, 2013.
[5] After one season with the San Antonio Scorpions, despite several international offers, Phelan elected to retire from professional football and pursue a career in Financial Planning.
He is the cousin of Gerard Phelan, the recipient of Doug Flutie's famed Hail Mary Pass versus Miami on November 23, 1984.