Regan played college soccer at Bradley University from 1999 to 2002, where he established himself as one of the best players in the program's history. After starting 20 games as a freshman, Regan was named second-team All-Missouri Valley Conference as a sophomore, after registering two goals and two assists from a defensive midfield position. Regan was moved to defense as a junior, and proved more than up to the task - he finished the year as a first-team All-MVC winner, and the team's co-MVP with Gavin Glinton. Regan remained at defense as a senior and performed even better, winning MVC Defensive Player of the Year while being instrumental in the team posting a 0.81 goals against average.
Professional
Upon graduating, Regan was selected 17th overall in the 2003 MLS SuperDraft by MetroStars of Major League Soccer. Regan was versatile, but not overly impressive in MLS. As a rookie, he appeared in 15 games, starting seven, at numerous positions in the defense and midfield. Regan received less playing time in 2004, playing in just 12 games. His hard work was rewarded with an expanded role in 2005, as he started 18 out of 20 matches. However, on March 1, 2006, Regan was released by MetroStars. One month later he was signed by his former Metro coach Bob Bradley at Chivas USA where he became a surprise starter. After the 2006 season, Regan was picked up by Toronto FC in the 2006 MLS Expansion Draft, but later traded to New York Red Bulls for forward Edson Buddle. He was waived by New York during the 2007 season. In the spring of 2008, Regan trained with Chicago Fire and appeared in a preseason games for his hometown club, but was not offered a contract. Later that season, he would, however, sign a 'one-day contract' with Toronto FC — who were missing nine players to international duty — in order to play in a game against his former club, Chivas USA. Regan eventually signed a deal with Toronto that kept him at the club until the end of the season. He retired following the 2008 season to become Toronto's head of scouting. He is also a "Soccer Operations & Scouting" instructor for the online sports career training school, Sports Management Worldwide, in Portland, OR.
