He took up the management position at York City in November 2021 and led the club to promotion out of the National League North via the play-offs at the end of the 2021–22 season.

[5] He was never handed a first-team debut at Vale Park and rejected manager John McGrath's £5-a-week offer following the conclusion of his six-month Youth Training Scheme contract.

[5] After leaving the club he spent a year working as a labourer for a pottery firm in Tunstall, before entering the insurance industry at the age of 19.

[7] Macclesfield played in the Football Conference for the first time in the 1987–88 season, and Askey scored 18 goals in 59 games as Town posted an 11th-place finish.

Askey made his only appearance for the England national semi-pro team on 6 March 1990 in a 0–0 draw with Wales at Penydarren Park in a friendly.

He reached ten goals in 47 games in the 1991–92 season as Macclesfield dropped down to 13th place; they did, though, retain the Cheshire Senior Cup with another 2–0 win over Witton Albion, this time at Prenton Park.

Askey scored 13 goals in 53 games in the 1993–94 season, including a hat-trick in a 6–1 win over Gateshead on 6 November; Macclesfield improved under new manager Sammy McIlroy, finishing seventh and picking up a cup double, winning the Bob Lord Challenge Trophy after beating Yeovil Town in the final and lifting the Staffordshire Senior Cup for the first time after defeating Wednesfield in the final.

It was at this point that, at the age of 34, he finally turned fully professional; speaking in 2020, he said,"I just thought, well we are playing teams like Man City, Stoke, Burnley and Preston.

Again consistent back in the Third Division in the 1999–2000 season, Askey was again named the club's Player of the Year after scoring 15 goals from 41 starts and four substitute appearances.

[22] He took the club to the third round of the FA Cup and 15th in the Conference Premier in the 2013–14 season, and was given a one-year rolling contract in the summer, though budget cutbacks meant that he lost the services of assistant manager Efe Sodje.

[citation needed] His Macclesfield team beat League One club Walsall in the first round of the 2016–17 FA Cup, becoming the only non-League club to beat an English Football League team in the opening round that season; Askey said "it is massive as it means we can pay the VAT bill this week".

[27] Macclesfield finished the season in ninth place and also reached the 2017 FA Trophy final at Wembley Stadium, where they were beaten 3–2 by York City.

[28] However, many of the squad left at the end of the season as Macclesfield were unable to compete financially with many of their divisional rivals; George Pilkington, Mitch Hancox and Danny Whitaker being some of the few players who remained.

[31] He appointed John Filan, whom he had previously worked with at Macclesfield, as his assistant,[32] whilst retaining the services of goalkeeping coach Danny Coyne and physiotherapist Chris Skitt as his backroom staff.

[31] He was dismissed on 12 November 2018 following a 1–1 draw with non-League Salford City in the FA Cup first round; he had won just five of his 21 matches in charge and left the club 18th in League One.

[33] "He inherited a squad that narrowly missed out on promotion to the Championship in May, but in reality, he had a big rebuilding job to replace last season's stars – Jon Nolan, Dean Henderson, Toto Nsiala, Alex Rodman, Stefan Payne, Ben Godfrey and Carlton Morris.

The timing of his appointment and the consequences of several high-profile departures in the transfer window with just days to go all made Askey's job even harder to emulate the club's success under Paul Hurst.

"On 4 February 2019, Askey was appointed manager of League Two club Port Vale on a contract until the end of the 2018–19 season, and named Dave Kevan as his assistant.

[36] There was no 'new manager bounce' as Vale fell to four defeats in his first four games, though his coaching methods eventually paid off with an impressive 2–1 win over promotion-chasing Mansfield Town on 9 March.

[39] Vale ended the season in 20th-place after securing 16 points from Askey's 16 games in charge and he signed a new three-year contract in May 2019, two weeks after Carol and Kevin Shanahan bought the club from Norman Smurthwaite.

[41][42][43] Coming into the club were goalkeeper Jonny Maddison; defenders Adam Crookes, Kieran Kennedy and Shaun Brisley; midfielders Scott Burgess, Ryan Lloyd, Callum Evans, Alex Hurst and Jake Taylor (on loan); wingers David Amoo and Rhys Browne; and strikers Mark Cullen, Richie Bennett and Jordan McFarlane-Archer.

[49] He signed seven players to replace the departures: Devante Rodney, Zak Mills, Danny Whitehead, Theo Robinson, David Fitzpatrick, Dino Visser and Harry McKirdy.

[57] He returned to Macclesfield, now a phoenix club in the North West Counties League Premier Division, to mentor manager Danny Whitaker on a short-term basis in August.

[66][67] Promotion was then secured by beating Boston United 2–0 in the play-off final and Askey said that "to do it in the centenary year and in the new ground [York Community Stadium], hopefully this is a new start for the football club".

[69] The club statement admitted that: "Given John's popularity and his incredible success last season, we understand that many fans may be upset and confused by this decision".

[77] On 6 June 2024, Askey was appointed manager of National League South side Truro City on a multi-year contract.