Mr. Underwood has been the Director of Bands at North Lincoln High School since the school opened in 2003. Prior to that, he was the Director of Bands at East Lincoln High School. Under his direction, his bands have performed twice in New York City's Carnegie Hall, three times at Bands of America Grand National Championships, the Hollywood Christmas Parade, and throughout the Southeast and Mid-Atlantic.

In 2001, Mr. Underwood was selected as Lincoln County's Teacher of the Year, and was a finalist for the Southwest Regional TOY. He has served as the President of the South Central District Band Association and as President of the North Carolina Bandmaster's Association. In 2008, he was selected as North Carolina's Citizenship Teacher of the Year by the Veterans of Foreign Wars.

In the Spring of 2011, the Band of Knight's Class of 2011 arranged the commission of a piece of music by nationally renowned composer Brian Balmages. The work titled "Joy in All Things" features the theme of North Lincoln's Alma Mater. This was a tremendous tribute to Mr. Underwood, but also an incredible contribution to the music of the international band world by the North Lincoln High School "Band of Knights."