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.

[3] 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 (the former MetroStars) for forward Edson Buddle.

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.