[1] While at Furman he was the leading goal scorer, a three-time all-conference selection, and the conference tournament MVP as a senior.
Once he moved to Albuquerque in 1997, he led the Geckos to the USISL D-3 Pro League Championship before coaching the club through its promotion to the A-League a season later.
On February 5, 2009, the Cleveland City Stars announced the hiring of Underwood to serve as the new head coach for the 2009 USL season.
[7] Underwood was named head coach for North East Stars in the TT Pro League on April 16, 2010.
[14] On March 3, 2021, Underwood was announced as the new head coach of National Independent Soccer Association side Stumptown AC ahead of the team's return from hiatus.