[3] He made his senior debut for the "Hatters" on 27 September 2011, coming on as a 75h-minute substitute for Michael Paton in a 4–2 defeat to Fleetwood Town at Edgeley Park.
[7] He was a key player for manager Jim Gannon in the 2012–13 campaign, scoring six goals in 45 appearances as County dropped into the Conference North with a second relegation in three years.
[11] This was his only appearance for West Ham and he left the Boleyn Ground when his contract was terminated on 28 January 2015 as part of a "massive cull of the development squad" by Terry Westley.
[17] On 31 July 2015, Whitehead signed a one-year deal with National League club Macclesfield Town after a successful trial period.
[4] On 8 January 2016, Whitehead signed a two-and-a-half-year-deal with League One side Wigan Athletic for an undisclosed fee; "Latics" boss Gary Caldwell cited the player's potential, saying "every club is on the lookout for fresh talent".
On 22 July 2016, he joined League Two club Cheltenham Town on a season-long loan after manager Gary Johnson saw him as a player who "will fit our game perfectly".
[25] Macclesfield went on to reach the 2017 FA Trophy final, though Whitehead was an unused substitute at Wembley Stadium as his teammates were beaten 3–2 by York City.
[32] He scored four goals from 44 appearances throughout the campaign and played in the National League play-off final as Salford secured a place in the EFL with a 3–0 victory over AFC Fylde at Wembley.
On 3 August 2020, Whitehead cancelled the last year of his contract with Salford and signed a two-year deal with League Two rivals Port Vale.
[36] The move reunited him with former Macclesfield boss John Askey, who brought Whitehead in to compete with Luke Joyce, Manny Oyeleke, Scott Burgess and Tom Conlon for one of three places in central midfield.
[42] He featured ten times for the "Robins" before he was recalled to his parent club on Christmas Eve after Vale suffered an injury and illness crisis.
[45] He scored one goal in eleven appearances for James Rowe's "Coasters", including the play-off semi-final defeat to Boston United at Mill Farm.