The centre back, who played for Tranmere Rovers and Stockport County, previously held the world record for the longest throw in football. This was 152 feet in a special challenge set-up at Prenton Park in 1998, beating the previous record held by Cardiff City's Andy Legg. When at Tranmere, he played in the 2000 Football League Cup Final. He was transferred to Stockport County for a fee of £120,000 in January 2002. Whilst playing for Stockport County against Grimsby Town, Challinor's tackle on striker Martin Pringle broke the leg of Pringle in two places, and effectively ended his career. Though Challinor only received a yellow card, Carlton Palmer, Stockport's player-manager, fined Challinor two weeks' wages and called the tackle "horrendous". Challinor joined Bury on loan for three months in January 2004., the move was made permanent during the summer. After spending four seasons at Bury as captain, he was forced to retire from professional football in May 2008 due to a knee injury. In October 2008, Challinor joined Colwyn Bay in the Northern Premier League Division One North, he captained the side to the play-offs in his first season where they lost out to Newcastle Blue Star on penalties. The following season the team, again captained by Challinor reached the play-offs and this time were promoted thanks to a 1–0 victory at Lancaster City in the final.
On 2 November 2011 it was announced that Challinor had been appointed the new manager of A.F.C. Fylde, in the Northern Premier League Division One North. He guided Fylde to the NPL First Division North championship in the season of his arrival and as a consequence was named Evo-Stik NPL Manager of the Year2011–12. In 2012–13, Fylde once again qualified for the Evo-Stik NPL Premier Division play offs but were defeated on penalties by Hednesford Town who took their place in the Conference North. Fylde did qualify for the FA Cup First Round proper, eventually being defeated by Accrington Stanley and also were victorious in the Lancashire FA Challenge Trophy at The Reebok Stadium, Bolton. The 2013–14 season saw Fylde gain promotion to the National League North after defeating Ashton United in the Evo-Stik NPL Premier Division play offs. They also retained their Lancashire FA Challenge Trophy with a 4–1 victory over rivals Chorley. In addition, they won the Doodson Sport League Cup with victory at Edgeley Park over Skelmersdale United. Their disciplinary record meant they won the Fair Play Award for the Premier Division and their overall record throughout the three leagues came out on top which saw them claim the Presidents Cup. They also had the best technical area marks for the Evo-Stik league to match the previous year's statistic. The year saw Fylde move to their highest rung of the pyramid and a fourth promotion in five years for Challinor. In 2016–17 Challinor clinched promotion as National League North champions, with a 3–0 victory over Boston United on 22 April 2017. In June 2017, he signed a new two-year contract with the club. On 12 October 2019 A.F.C. Fylde announced that it was parting company with him as the manager.
Hartlepool United
On 11 November 2019, Challinor was officially appointed as manager of Hartlepool United.
