Wilford graduated from Fork Union Military Academy and played football for Armstrong High School in Richmond.
However, Wilford is probably most remembered for dropping a 2-point conversion pass that would have tied the game with about 6 minutes left against #1 Miami in 2001.
The Dolphins converted Wilford to tight end during the 2009 offseason, but released him prior to the regular season on August 24.
On May 21, 2010, he cut his hair which had been growing for over six years in recognition of Jacksonville's Wolfson Children's Hospital cancer unit, as a donation.
On Thursday September 16, 2010, the Jaguars re-signed Wilford back to the 53 man roster stating that he provides a veteran who is familiar with the system and can contribute on special teams.
Early in the morning on January 14, 2011, Wilford was arrested for inappropriately touching a female bartender at the Ritz Club in Jacksonville Beach.
[citation needed] Wilford currently volunteers as an assistant football coach at Tocoi Creek High School in Jacksonville, Florida.