After scoring a hat trick in a CONCACAF Champions Cup game against the Chicago Fire on 17 March 2004, Glen was bought by the MetroStars of Major League Soccer.

In his first season Glen made a significant impact, registering six goals and two assists as he competed for playing time on a very crowded MetroStars front line.

After briefly returning to Trinidad to play for San Juan Jabloteh in 2007, Glen trialled Leeds United from the English Coca-Cola Football League One in January 2008,[2] but was not offered a contract.

Glen went on trial with Major League Soccer side San Jose Earthquakes in May 2009 and successfully signed a one-year deal with the club shortly thereafter.

Much of Glen's time with the Earthquakes was plagued by injuries, and following a statistically disappointing 2010 season his contract was not renewed by the San Jose club.

Trinidad & Tobago were eliminated in the first round after losing to England and Paraguay, but Glen's performances during the tournament earned him praise and recognition.

[19] As a member of the squad that competed at the 2006 FIFA World Cup in Germany, Glen was awarded the Chaconia Medal (Gold Class), the second highest state decoration of Trinidad and Tobago.