Dave Challinor was a player at Edgeley Park in 2002 when Stockport County fell out of the second tier, a relegation that sent the club tumbling through the Football League and into non-league regional football for years to come. Now, a quarter of a century later, the manager stands one match away from leading them full circle back to the Championship—the pinnacle of English football's second tier—when Stockport County takes on Bolton Wanderers in Sunday's League One play-off final at Wembley Stadium in London.
It is a remarkable trajectory for both clubs, each carrying the weight of long exiles from the second-tier football they once knew. Bolton's recent past is sharper in memory: they nearly collapsed entirely in 2019, edging toward administration before being rescued by a takeover. They clawed back to League One immediately in 2020-21, then mounted two consecutive runs to the play-offs under Ian Evatt, only to suffer a crushing 2-0 defeat to Oxford at Wembley just two seasons ago. That loss, Evatt suggested afterward, came down to "fear." But the mood has shifted under new manager Steven Schumacher, who took charge in January 2025. Defender George Johnston captured the difference: "It almost felt like [before] 'right, that job's done, on to the next job'. But this time it's definitely half-job done and we're fully focused on the next game and to really celebrate once we do get the win."
Challinor's career arc reads like a masterclass in steady ambition. In 16 seasons as a manager, he has finished outside the play-offs just once—the Covid-interrupted 2019-20 season—and has compiled an extraordinary record of seven promotions and four league titles across Colwyn Bay, AFC Fylde, Hartlepool United, and Stockport County. When asked about his promotion pedigree, Challinor remained humble yet resolute: "A whole host of people work so hard and go through so much to give ourselves the opportunity and we've got that opportunity. So we have to do everything now to make sure we do what we can to grab it."
That opportunity comes after Stockport's gradual resurrection since Mark Stott took over the club in 2020. The owner has stewarded the club's return from the wilderness of the National League North back into the professional pyramid—a journey that would have seemed impossible just six years ago. Challinor himself saw that full arc: "I played in the last Championship game that Stockport County played in, and from that point on, the supporters have been through relegations, promotions, administration, all sorts, with the club going back out of the Football League into the National League North. Since Mark came in six years ago, everything's been on the up since then, and we've got ourselves to this point."
Bolton will face Wembley without their captain, Eoin Toal, who suffered a high-grade hamstring tear during their semi-final victory over Bradford—a significant injury that will sideline him for the crucial match. The two sides have split their recent meetings: Stockport won 2-0 at the start of the season, while Bolton earned a 2-2 draw in their April rematch.
Come Sunday, both clubs will chase redemption and return. For Stockport, it means finishing what they started two and a half decades ago. For Bolton, it means finally breaking free from their years of second-tier exile. One team will get their prize.