He spent five years with the club and made over 200 appearances in all competitions before he switched to Port Vale in June 2006.

He helped the club to the League Two title in 2010–11 and also won himself a place on the division's PFA Team of the Year.

Whitaker led phoenix club Macclesfield to the North West Counties Premier Division title at the end of the 2021–22 season before losing his job in October 2022.

Whitaker was a Manchester United junior,[4] and spent time at both Bradford City and local side Wilmslow Albion before signing with Macclesfield Town.

However, manager David Moss was highly dismissive of such speculation, saying: "Quite frankly, I am sick and tired of reading about players who have just signed two-year contracts but want to get away.

He scored just four goals in the 2004–05 season, though manager Brian Horton was still keen to hold on to him, despite nine others being deemed unworthy of a new deal.

[16][17] On 20 June 2008, he turned down the chance to stay at Vale, and instead opted to join Oldham Athletic, still in League One.

He was an unused substitute as Chesterfield beat Swindon Town in the final of the Football League Trophy at Wembley Stadium.

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.

[25] 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.

[27] On 8 October 2018, Whitaker and Neil Howarth were appointed as Macclesfield Town's joint-caretaker managers following the dismissal of Mark Yates.

[32] He won his one game in charge, before returning to his coaching duties once Daryl McMahon was appointed as manager four days later.

[5] He came out of retirement to sign a one-year playing contract with Macclesfield on 15 September 2020,[5][37] but the club was liquidated a day later.

[39] He was also registered as a player, and played himself in the first competitive match for the new club on 31 July 2021, in a 1–0 win at home to Burscough in the North West Counties League Premier Division.