He helped Stoke reach the 2011 FA Cup final, where the team finished runners-up to Manchester City.

[4] He progressed through the ranks, making his first-team debut in a 2–0 win over Luton Town in the Football League Trophy on 7 December 1999.

[9] Although he received his first-team opportunities, he found himself in a competition with Matt Murphy and other midfielders for the central role.

[10] Despite being sidelined on two occasions, due to suspensions,[11] Whitehead played in 23 matches in 2000–01 season,[12] as Oxford suffered relegation to the Third Division.

[16] However, halfway through the season, Whitehead, along with Chris Hackett were subjected to criticism by manager Ian Atkins for unprofessionalism over refusing to do the club's fitness programme, which were denied by the pair, who stated the whole thing was a misunderstanding.

[38][39] Manager Graham Rix revealed that Whitehead would have been appointed as Crosby's successor as captain if he signed a new contract with the club.

[41] Upon signing a three–year contract with the club, he revealed that his ambition and desire to play at a higher level was why he joined Sunderland.

[42] Sunderland were ordered to pay £150,000 to Oxford at an FA tribunal, to compensate for the time and money put into his development.

[44] Whitehead made his Sunderland debut, coming on as a late substitute for Ben Clark, in a 2–0 loss against Coventry City in the opening game of the season.

[60] He scored a swerving 30 yards (27 m) free kick past then-England goalkeeper Paul Robinson in a 3–2 defeat against Tottenham Hotspur at White Hart Lane on 3 December.

[66] Whitehead then scored his first goal of the season against West Bromwich Albion, in a 2–0 win during which he was named as man of the match.

[84] Ahead of the 2008–09 season, Whitehead was linked to a move away from Sunderland, as newly-promotion Premier League side Stoke City made a £3 million bid on him.

[99] Whitehead scored his first goal for Stoke when he converted winger Matthew Etherington's cross in the 86th-minute in a 3–1 FA Cup fourth-round win over Arsenal at the Britannia Stadium on 24 January 2010.

[100] Whitehead was sent off against Tottenham Hotspur in March 2010 in a decision which drew referee Mike Dean heavy criticism from Tony Pulis and Matthew Etherington.

[104] Towards the end of 2010–11, Whitehead lost his place in the starting eleven to a resurging Glenn Whelan, making some cameo appearances from the bench.

[107] He then made his 100th appearance for Stoke on 3 November 2011 in a UEFA Europa League match against Maccabi Tel Aviv, scoring the first goal in a 2–1 victory.

[111] He remained back-up to Glenn Whelan for the remainder of the season, being used mainly as a substitute, although he was assigned as a stand-in right-back in the absence of Andy Wilkinson and Ryan Shotton.

[114] Manager Tony Mowbray revealed that Whitehead's experience of gaining promotion from the Championship twice was the key reason in signing him.

[127] This was due to added competition for the defensive midfield position with Richard Smallwood, Grant Leadbitter and Adam Clayton.

[128][129] However, in a 4–0 win over Brentford on 20 September, he was sent–off "for an over the top tackle", leading the referee giving him a straight red card.

At the end of the season, Whitehead left Middlesbrough as manager Aitor Karanka could not guarantee him game time.

[147] A month later, on 23 January, Whitehead returned to the first-team from injury, coming on as a late substitute in a 2–1 loss against Brighton & Hove Albion.

[161] He made his first appearance of the 2017–18 season, where he started the whole game, in a 2–1 win over Rotherham United in the second round of the League Cup on 23 August.

[162] Then, on 30 September, Whitehead made his first Premier League appearance – his first in four years – as a late substitute, in a 4–0 loss against Tottenham Hotspur.

[165] He made his last appearance for the club (and his football career), coming on as a late substitute, in a 1–0 loss against Arsenal in the last game of the season.

[168] On 16 November 2019, Whitehead joined Sam Ricketts' backroom staff at League One side Shrewsbury Town, replacing Joe Parkinson as first-team coach.

[172] Having helped Vale to win promotion at the end of the 2021–22 season, he moved to Turkey in July 2022 to coach alongside Adam Murray at Süper Lig champions Beşiktaş.

[175] Following the sacking of Mark Hudson on 14 January 2023, Whitehead was placed in interim charge of the first-team at Cardiff City.

[176] In the 2023 pre-season, Ismaël was appointed manager at Championship side Watford, and Whitehead moved to work there with him as assistant head coach.

[184] During his time at Stoke City and Huddersfield Town, Whitehead resided in Cheshire with his wife, Louise, and their two sons, Olly and Harry.