Henry played college football for the Florida Gators, earned consensus All-American honors, and won the Ray Guy Award.

[4] Memorably, Henry also assumed place-kicking duties when starting place kicker Caleb Sturgis was injured, and kicked the 37-yard, game-winning field goal in the Gators' 34–31 overtime victory over the rival Georgia Bulldogs while several Bulldog assistant coaches attempted to distract him from the sideline.

[8][9] After he was not selected in the 2011 NFL draft, Henry signed as an undrafted free agent with the Philadelphia Eagles.

Henry committed a Monday Night Football blunder against the Chicago Bears in a Week 9 loss, in which he botched a fake punt, and his pass was underthrown.

[12] Henry was signed by the Buccaneers on February 13, 2013, and was competing for the starting spot against Michael Koenen.