He played college football at Rutgers and was selected by the Jacksonville Jaguars in the seventh round of the 2009 NFL draft.

Underwood was also a member of the New England Patriots, Tampa Bay Buccaneers, and Carolina Panthers in the NFL.

He also played for the Hamilton Tiger Cats and Montreal Alouettes of the Canadian Football League (CFL).

After the season, he was the recipient of the Loyal Knight Award, honoring the Rutgers player whose character and dedication have proved resilient in his pursuit of excellence.

On November 8, 2011, Underwood was signed to the 53 man roster to boost a beleaguered kick return squad.

[15] On October 21, 2012, Underwood caught his first touchdown pass of his career in a losing effort to the New Orleans Saints.

[17] On April 2, 2015, Underwood signed with the Hamilton Tiger Cats of the Canadian Football League (CFL).

[21] Shortly after retiring from playing professional football, Underwood was hired as the wide receivers coach for Lafayette for the 2018 season.

[25] On February 3, 2025, the Dallas Cowboys hired Underwood to serve as their assistant wide receivers coach.