Colwyn Bay Challinor was appointed as player-manager at Northern Premier League Premier Division club
Colwyn Bay on 28 May 2010. He was assisted by former teammate
Colin Woodthorpe. During their first season in management, they led Colwyn Bay to runners-up in the Northern Premier League Premier Division and a place in the play-offs. Victories over
North Ferriby United and
FC United of Manchester secured the club promotion to the
Conference North. The club also won the
North Wales Coast Cup, with victory over
Flint Town United in the final on penalties. The club won the Fair Play Award for the fewest disciplinary points through the season and Challinor was named manager of the month for March, April and May 2011.
AFC Fylde On 2 November 2011 it was announced that Challinor had been appointed the new manager of
AFC 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 Year 2011–12. 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. In Fylde's debut National League campaign, the club reached the play-offs but lost 2–1 to
Boreham Wood. The
2018–19 season saw Fylde reach both the
play-off final and
FA Trophy final. Having been defeated 3–0 by
Salford City in the play-off final, Fylde returned to
Wembley Stadium the following week to beat
Leyton Orient 1–0 and lift the
FA Trophy for the first time in the club's history. On 12 October 2019, after spending eight years as manager, Fylde announced that it was parting company with him as the manager, with the side in the relegation places on goal difference.
Hartlepool United On 11 November 2019, Challinor was appointed manager of
National League side
Hartlepool United with the club in 13th place. In his first full season in charge, Challinor guided Hartlepool to a 4th placed finish and a place in the 2020–21
National League play-offs. In the play-off eliminator, Hartlepool defeated
Bromley 3–2, scoring three goals in seven first-half minutes before Bromley scored two in the second half, ultimately proving to not be enough. In the semi-final, they travelled to
Stockport County where
Rhys Oates scored with fifteen minutes left to book Hartlepool's place in the final. On 20 June 2021, Hartlepool faced
Torquay United in the
2021 National League play-off final at
Ashton Gate Stadium. On 24 September 2021, Challinor signed a new three-year contract to remain as manager. On 1 November 2021, Challinor announced his intentions to step down from the position. In a club statement, Hartlepool stated their dissatisfaction with the way Challinor departed the club: "As a club, we were disappointed the first approach did not come direct to the club. Also that this was so soon after Dave signed a new three-year contract." In an interview with Stockport following his arrival, Challinor said that "It's been ridiculously difficult (to leave Hartlepool), once the interest came in (from Stockport) there was always going to be an attraction but the affinity I built up with the fan base there was amazing and that was the biggest tie that I had to get over".
Stockport County On 2 November 2021, Challinor was appointed manager of
National League side
Stockport County with the club in 9th position, ten points from 1st place. Challinor was awarded the National League's Manager of the Month award for January 2022 after six wins from six in all competitions that saw Stockport finish the month top of the league. He would lose only one of his first 23 matches with Stockport. Following promotion, Challinor was named as the National League Manager of the Season. He also won the Manager of the Month award for February 2023 after winning five games from six. Stockport missed out on automatic promotion to
EFL League One on the final day of the season, finishing 4th and qualifying for the play-offs. After defeating
Salford City in the semi-final, Stockport lost on penalties in the
play-off final to
Carlisle United. On 5 July 2023, Challinor signed a new three-year deal with Stockport. In August 2023, rumours emerged that Challinor had been interviewed for the vacant manager's job at League One club
Charlton Athletic. Having remained at Stockport, he received two successive Manager of the Month awards, for September and October, extending a club-record winning run to twelve matches. At the end of the
2023–24 season, Stockport were promoted to League One as champions. This was their first Football League division title since
1966–67. ==Personal life==