Rookie season - Whitehead was signed as an undrafted free agent by the Dallas Cowboys after the 2015 NFL Draft. He made the team as one of the players that was looked upon to replace the departed Dwayne Harris special teams production.
In the 2016 preseason opener vs. the Rams — the first NFL game in Los Angeles in more than 20 years — Whitehead returned the opening kickoff 101 yards for a TD. He also had one catch for 6 yards and one rushing attempt for 11 yards.Although Cole Beasley was the assigned punt returner early in the season, because he provided better ball security, Whitehead was given opportunities until earning the returner role for the final six games. He only averaged 5.8 yards per attempt as a punt returner, but showed glimpses as a kickoff returner (28.3 yards avg.), like his 79-yard kickoff return against the Philadelphia Eagles or his key 46-yard kickoff return against the Washington Redskins to set up the game-winning field goal with 14 seconds left. He also was used on offense with special runs designed for him. In the sixth game of the season against the New York Giants, he set a franchise record for a wide receiver with 4 rushing attempts. He finished the 2015 season with 10 rushes for 107 yards and 6 receptions for 16 yards.
In week 6 versus the Green Bay Packers, Whitehead caught a career-long 35-yard reception as well as running the ball a season-long 26 yards.
