Whitehead played junior rugby league for West Bowling before being signed by his hometown professional club Bradford Bulls in 2005.

[4] Whitehead made his Super League début in June 2009 against Wakefield Trinity, and went on to make seven appearances in the final ten games of the season.

Whitehead scored against Castleford (2 tries), Hull Kingston Rovers (1 try), Leeds (1 try), Crusaders (1 try), Harlequins RL (1 try), Salford (1 try), Wakefield Trinity (1 try) and Dewsbury (1 try).

In August 2011, Whitehead received a five-game suspension after being charged with biting Hull Kingston Rovers forward Jordan Cox.

Whitehead scored tries against Wakefield Trinity (4 tries), St. Helens (1 try), Salford (1 try), Doncaster (3 tries), Leeds (2 tries), Wigan (1 try), London Broncos (1 try), Warrington (1 try) and Hull Kingston Rovers (1 try).

[9] Whitehead signed a two-and-a-half-year deal with Catalans, and he made his début for the club in July 2013 against London Broncos.

(1 try), Wakefield Trinity (5 tries), Huddersfield (1 try), Widnes (3 tries), Hull Kingston Rovers (2 tries), London Broncos (2 tries), Bradford Bulls (2 tries), Wigan (1 try) and Castleford (1 try).

[citation needed] On 8 April 2015, Whitehead signed a two-year contract with National Rugby League side Canberra Raiders starting in 2016.

Whitehead credits his ability to adapt to the Australian style of play on personal fitness guru Chris Anderson.

[17][18] Whitehead played a total of 22 games for Canberra in the 2022 NRL season as the club finished 8th on the table and qualified for the finals.

[19] Whitehead played a total of 23 matches for Canberra in the 2023 NRL season as the club finished 8th on the table and qualified for the finals.

[20] In round 9 of the 2024 NRL season, Whitehead came back into the Canberra team after a lengthy injury and scored two tries for the club in their comeback victory over Manly.

[22] On 11 Jul 2024 it was reported he had re-joined Catalans Dragons on a 1-year deal[23] In 2014, Whitehead was selected in England's 2014 Four Nations squad.