named in the PFA Team of the Year, along with teammates Craig Davies and Tommy Lee. The following season, 2011–12, the "Spireites" struggled at the bottom of League One, and Whittaker lost his first team place in the new year. He was an unused substitute as Chesterfield beat Swindon Town in the final of the League Trophy at Wembley Stadium. He was offered a new one-year contract by the club in May 2012. He made 34 appearances in the 2012–13 campaign, and was not offered a new contract by manager Paul Cook. Return to Macclesfield Whitaker re-signed with Conference Premier club Macclesfield Town in August 2013. He made 49 appearances for John Askey's "Silkmen" across the 2013–14 campaign. He agreed to a new one-year deal in July 2014. He scored six goals in 30 games in the 2014–15 season. He scored eight goals in 50 appearances in the 2015–16 campaign as Macclesfield finished in tenth position and signed a new one-year contract in July 2016. He made 55 appearances across the 2016–17 campaign, including in the 2017 FA Trophy Final at Wembley Stadium, where Macclesfield were beaten 3–2 by York City. He scored eight goals in 45 appearances in 2017–18 as Macclesfield won promotion back to the Football League as champions of the National League. On 8 October 2018, Whitaker and Neil Howarth were appointed as Macclesfield Town's joint-caretaker-managers following the dismissal of Mark Yates. They remained in charge until Sol Campbell was appointed as manager on 27 November. He scored three goals in 26 games as Macclesfield secured their safety at the end of the 2018–19 season. He announced his retirement in July 2019. He again was appointed as Macclesfield Town's caretaker-manager following the resignation of Sol Campbell on 15 August 2019. He won his one game in charge, before returning to his coaching duties once Daryl McMahon was appointed as manager four days later. McMahon resigned on 3 January 2020, leaving Whitaker to once again step in as caretaker-manager. He remained in the role for 13 days until the appointment of Mark Kennedy. He stayed on in the role of assistant manager under first Kennedy and then Tim Flowers. He came out of retirement to sign a one-year playing contract with Macclesfield on 15 September 2020, but the club was liquidated a day later. Managerial career Whitaker was appointed as the first ever manager of Macclesfield Town's phoenix