The romance of knock-out football is normally associated with the muddy slopes of winter rather than swish new all-seater citadels in summer, and with the FA Cup instead of the uncharismatic rival we must now call the Worthington Cup. Askey, by scoring two late goals to give Macclesfield a 3-1 first-leg lead over nearby Stoke, has set up an opportunity to break the mould at the Britannia.
Although both teams are now in the Second Division, Macclesfield's fans could be excused for relishing the prospect of a giant-killing. When Askey first joined them, 12 years and more than 500 appearances ago, they were content to be a power in the Northern Premier League whereas Stoke harboured hopes of regaining their recently surrendered top-flight status.
But the Askey clan's big night out is more than simply the familiar tale of a player straining to scupper the side he supports. It is a story which mirrors Macclesfield's own rise in terms of the 33-year-old striker's persistence in the face of adversity. Remarkably, he is now in his fourth spell with the Cheshire club, having been released by no fewer than three of Sammy McIlroy's predecessors.
He had started out as a YTS boy with Stoke's neighbours, Port Vale, with whom his father, Colin, reached the FA Cup semi-finals in 1954. Robbie Earle was the only one of his contemporaries taken on as a professional, so Askey's brother Bob, who was turning out for Macclesfield, invited him to the Moss Rose.
"Brian Booth was the manager, but he let me go," Askey recalls. "I was just a kid and probably too young to appreciate what was required. Then Neil Griffiths invited me back to play in the FA Cup against Hartlepool because they were short of players. I scored but he never came back to me, which I found a bit surprising.
"I'd gone back to the Vale, playing for the reserves and for a team called Milton United that my dad ran, when Peter Wragg asked me back to Macc. My brother had to talk me into it because I felt a bit let down. I did all right but eventually they freed me again and I thought that was it."
Amazingly, injuries and suspensions led to his joining for a fourth time. Neither Askey nor Macclesfield have looked back. "It's been unbelievable, winning the Conference then going straight through the Third Division. Sammy's the best manager I've had. He always encourages you to get the ball down and play."
This summer, half a lifetime after his dreams of earning a living from football were dashed, Askey finally gave up his job as an insurance agent and signed a two-year contract as a full-time player. "I couldn't have competed as a semi-pro at this level, where you're playing the likes of Manchester City, Fulham and Stoke.
"It's just like having two years off from work. I've passed all my exams so I'll be able to go back. I'm enjoying the training and I'm probably fitter than ever. When I realised Macc were playing Stoke three times in eight days [the clubs also met in the League on Saturday, Brian Little's team winning 2-0] it made me go even harder in pre-season to make sure I was in the side."
Askey was in Macclesfield's line-up 10 years ago when, with a visit from Tottenham awaiting the winners, they lost an FA Cup tie at Vale Park to "a crabby late goal". He has also had a trial with Everton, played at Wembley in the FA Trophy final and against the national team in Japan for a non-League select XI, but considers the current "series" with his childhood heroes as the pinnacle of his career.
"I've always followed Stoke, especially around the time when local products like Garth Crooks, Adrian Heath, Lee Chapman and Paul Bracewell were playing. So it's fantastic to be facing them in competitive fixtures.
"The first match was incredibly open. The statistics showed 30-odd shots on goal and I was fortunate enough to score a couple. It was different at Stoke - they came out with more determination and for some reason we weren't up for it. We'll have to do better in the second leg because we've lost both our Second Division games and we don't want a rot to set in."
After the first meeting, Askey joked about retiring. Now, in keeping with the conventional wisdom of his "new" profession, he warns that it is only half-time in the tie.Reuse content