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Heckingbottom was appointed head coach of Scottish Premiership club Hibernian on 13 February 2019. The club went on an unbeaten league run, and Heckingbottom won the Premiership manager of the month award for March 2019. Two days later, Heckingbottom won his first Edinburgh derby match as Hibs manager against Hearts at Tynecastle, Hibs' first away derby win for six years. Hibs finished in fifth position, but Heckingbottom was unhappy that the team "downed tools" in the last few matches of the season.

Hibs only won one of their first 11 league matches in the 2019/20 season. Heckingbottom was sacked by Hibs on 4 November following a 5–2 defeat by Celtic in a League Cup semi-final, with the team sitting in 10th place in the league.

The good form and results continued for the first half of the 2016-17 Championship season as the club ended 2016 in 9th position in the table. Heckingbottom was awarded Sports Hero of the Year by The Yorkshire Post. Heckingbottom signed a new rolling contract at Barnsley on 2 February 2018, but he would leave the club days later to take a similar position with Leeds United.

On 6 February 2018, Heckingbottom was announced as the new head coach of Leeds United on an 18-month contract. Leeds lost his first match as head coach, 2–1 against Sheffield United, and finished 13th in the 2017–18 EFL Championship league table. Heckingbottom blooded youngster Bailey Peacock-Farrell as first choice goalkeeper and also gave debuts to academy players Tom Pearce, Paudie O'Connor, Hugo Díaz and Ryan Edmondson. Heckingbottom integrated further academy players with the first team during a post-season tour of Myanmar. Heckingbottom was sacked by Leeds on 1 June 2018, after just four months with the club. He was replaced by Marcelo Bielsa on 15 June.

After retiring as a player, Heckingbottom trained as a coach. He obtained a position with Barnsley's development squad and, after a successful spell as caretaker manager in which the club won promotion and the EFL Trophy, he was appointed manager in 2016. In February 2018 he moved to Leeds United, but he was sacked by Leeds during the 2018 close season after 16 games in charge. Heckingbottom then managed Scottish Premiership club Hibernian, but was sacked in November 2019.

After working as a coach with Barnsley's Development Squad, Heckingbottom took caretaker charge after Danny Wilson was sacked by the club in 2015. He was again made caretaker after the departure of Lee Johnson to Bristol City in 2016. During the latter spell, he guided Barnsley to a 3–2 win against Oxford United in the Football League Trophy final and promotion by beating Millwall 3–1 in the League One play-off final. His success as caretaker, leading Barnsley to their first cup final victory since 1912 and promotion to the Championship, led to him being appointed head coach on a permanent basis.

Heckingbottom was well favoured under both Wednesday managers Chris Turner and Paul Sturrock, making a total of 41 appearances at left back in his first season – more than any other player that year. He also scored four goals, helping The Owls to promotion to the Championship via the League One play-off final at the end of the 2004–05 season. Due to an injury sustained in pre-season he was put out of contention for the first 16 games of the 2005–06 season. When he returned to fitness, new signing John Hills had begun to make the left back spot his own. An injury to Hills left Heckingbottom able to re-stake his claim on the team, but he only managed a 4-game streak before once again succumbing to injury, this time Peter Gilbert taking his place in the squad. Sturrock allowed Heckingbottom a chance to prove himself in an FA Cup Third Round game against Charlton Athletic. He scored both of Wednesday's goals in the 4–2 defeat at Hillsborough, though this was not enough to establish himself as the club's first choice left back.

Heckingbottom took the opportunity to gain an academic understanding of football coaching, to set his CV apart from other managers competing for jobs. He completed his BSc (Hons) Sports Coaching in 2013, followed by an MSc in Sport Coaching in 2016.

Heckingbottom signed for Gateshead on a permanent basis on 26 May 2010. He made 22 appearances in all competitions during the 2010–11 season before he was released on 4 May 2011.

Bradford opted against offering Heckingbottom a contract extension, and he left the club in May 2009.

Heckingbottom signed for Conference National side Mansfield Town on 2 June 2009, marking his first foray into the game outside of The Football League. He sustained a hamstring injury in pre-season and did not play until October, in a 1–0 win over Forest Green Rovers, 11 months from when he last played a game of football. He became a regular in the Mansfield line-up. He scored his first and only Mansfield goal against Crawley Town on 14 November 2009. On 1 February 2010, Heckingbottom joined Gateshead on loan until the end of the season. making his debut on 13 February away at Hayes & Yeading United.

In July 2007, Heckingbottom returned to Bradford City on loan until 1 January 2008. He played in all 23 league games during his loan spell, missing only an FA Cup tie against Tranmere Rovers after he was suspended following a red card in a 1–1 draw with Stockport County. A week after his loan deal expired, his contract at Barnsley was cancelled by mutual consent and he signed a permanent 18-month deal at Bradford. He missed his first league game of the 2007–08 season with four games left, when an ankle injury prevented him for playing against Brentford on 12 April 2008. Heckingbottom's place was taken by Luke O'Brien, who made his Bradford debut, in a 2–2 draw.

He played in the club's first nine league games of the 2008–09 season, but was sent off in a 1–1 draw with Luton Town for two bookable offences. His place was again taken by youngster O'Brien, and although Heckingbottom returned for an FA Cup game against Milton Keynes Dons, he suffered a tendonitis injury, which kept him out for five months.

On 13 January 2006, Heckingbottom was sent on loan, with a view to a permanent move, to his boyhood club Barnsley. He played an important part in the club's promotion campaign and win over Swansea City in the League One play-off final, scoring in the 4–3 penalty shootout victory that secured their promotion to the Championship. Heckingbottom played in 31 games for Barnsley the next season, as they comfortably avoided relegation. He scored once during his spell at Barnsley, in a 1–0 win over Tranmere Rovers on 18 February 2006.

Heckingbottom made just 16 appearances for Norwich, including only 7 starts, resulting in him cancelling his contract with the club by mutual consent after one year. He subsequently signed for Bradford City in July 2003, where he was named their Player of the Year at the end of his first season. Bradford, however, were relegated to League One at the end of the 2003–04 season, and Heckingbottom left to join Sheffield Wednesday during the close-season.

Heckingbottom was born in Barnsley and grew up in nearby Royston. As a child, he was a season ticket holder at the town's football club, along with his grandfather. He started his football career at Manchester United as a trainee, but joined Sunderland in 1995 after failing to gain a professional contract. He had loan spells at Scarborough, Hartlepool United and Darlington, without featuring for Sunderland, before joining Darlington permanently in 1999. He made 126 appearances, scoring 6 goals, before catching the attention of First Division side Norwich City, who signed him in 2002 on a three-year contract.

Paul Heckingbottom (born 17 July 1977) is an English football coach and former player. Heckingbottom played as a defender for several English clubs, including Sunderland, Scarborough, Hartlepool United, Darlington, Norwich City, Bradford City, Sheffield Wednesday, Barnsley and Mansfield Town.