Blackpool 's finishing positions in
the Football League under Grayson. 2008's finish of 19th surpassed the previous high of
1971–72, under
Bob Stokoe Grayson moved into coaching in the
2004–05 season, managing the
reserve squad at
Bloomfield Road with some success. He was named
caretaker manager of the first team in November 2005, following the departure of
Colin Hendry. After diverting Blackpool away from relegation that season he was given the job on a permanent basis for the start of the
2006–07 season. Grayson retired from playing at the end of the
2005–06 season to focus purely on the managerial side of the game. In late 2006, he led Blackpool to only one defeat in fourteen league games, a sequence that included five wins out of six, resulting in their appearance in the four
play-off positions. The run also brought attendances of more than 7,000 to Bloomfield Road. This led to Grayson being awarded the
Manager of the Month award for December. On 6 January 2007, he guided Blackpool to the fourth round of the
FA Cup for the first time in 17 years, after beating
Aldershot Town 4–2 at Bloomfield Road. They were knocked out by
Norwich City, who beat them 3–2 after
extra time, in a
replay at
Carrow Road on 13 February, narrowly missing out on a trip to London to face
Chelsea in the last sixteen. Grayson received his second League One Manager of the Month award of the 2006–07 season in May 2007. Two days later, on 5 May 2007, Grayson guided Blackpool to a final placing of third, and thus a place in the play-offs. Blackpool beat
Oldham Athletic 5–2 on aggregate over the two legs of the
play-off semi-final. They met
Yeovil Town in the final at the newly renovated
Wembley Stadium on 27 May and won 2–0, securing promotion to the
Championship. It was their tenth consecutive victory, a new club record. This was extended in Blackpool's first game in the Championship with a league win over
Leicester City and a victory against
Huddersfield Town in the League Cup. In October 2007, Grayson guided Blackpool to the fourth round of the League Cup for the club's first time in 35 years. They were drawn against
Tottenham Hotspur at
White Hart Lane, where Spurs won 2–0. In December 2007 Grayson signed a two-and-a-half-year contract, following two years working without a formal contract. In May 2008, Blackpool finished nineteenth in the Championship. Grayson was heavily linked with the vacant managerial post at
Leeds United, with whom he started his playing career, following the dismissal of
Gary McAllister in December 2008, but Blackpool refused permission for Leeds to speak to Grayson. Despite this Grayson tendered his resignation, which the Blackpool board did not accept, and he was announced as Leeds United's new manager. The two clubs ultimately settled the dispute for an undisclosed fee.
Leeds United Grayson's first game in charge was at
Elland Road on Boxing Day against one of his former clubs,
Leicester City, who were top of
League One. Leeds were sitting in 9th place, on the back of five straight defeats, but a late equaliser from
Robert Snodgrass gave Grayson's new club a 1–1 draw. He recorded his first victory, a crucial 3–1 win away at
Stockport County two days later. Grayson's side also earned Leeds a replay against Premiership opposition
Tottenham Hotspur after a 2–2 draw at White Hart Lane. Grayson's Leeds side was promoted on 8 May 2010 after beating
Bristol Rovers 2–1 in their final game coming back from 0–1 with only 10 men. The win saw Leeds finish the season in second place, and earn automatic promotion to The Championship. Grayson reached his 100th game managing Leeds in the 2–1 win against
Middlesbrough. Grayson was rewarded with his first Manager of the Month award while in charge at Leeds United for the month of December 2010. During that month he oversaw his Leeds team unbeaten in the league, winning three games and drawing two, including a 2–0 home win over league leaders QPR. After a dip in form, Leeds dropped out of the playoff places and finished the season in 7th place. On 1 February 2012, Grayson was dismissed by Leeds United due to lack of results he was getting. A Club Statement said: "We have 18 games to go this season and are still within touching distance of the Play-Offs, but felt with the transfer window now closed we needed to make the change at this time in the belief that a new managerial team will be able to get more out of the existing squad of players and make the difference". His last result was a 4–1 defeat to Birmingham City on 31 January 2012.
Huddersfield Town On 20 February 2012, just five days after
Lee Clark was dismissed as manager, Grayson became the new manager of
League One club Huddersfield Town on a -year deal. His first game in charge of the Terriers was in their 2–0 home victory over
Exeter City when both defender
Jamie McCombe and leading striker
Jordan Rhodes scoring. He also introduced Icelandic midfielder
Joey Guðjónsson to the squad for the first time all season. While remaining unbeaten, his next five games in charge proved to be mostly unspectacular, resulting in four draws against
Stevenage,
Bury,
Rochdale and
Colchester United, also defeating
Hartlepool United in a 1–0 home victory. The early pattern of these results remained similar to those of the previous manager,
Lee Clark, who managed a number of draws, which were held responsible for the Terrier's inability to cement a place in the automatic promotion spots. With 10 games remaining, Town occupied 4th position in League One, contrary to the chairman
Dean Hoyle's brief urging the club to reach one of the top two positions. On 26 May 2012, Grayson led Huddersfield to
play-off victory over
Sheffield United, gaining promotion to the Championship. Grayson's first match in charge of Huddersfield in the Championship came on 17 August 2012, a 1–0 defeat away to
Cardiff. His first Championship win as the club's manager was on 25 August 2012, a 2–0 home victory against
Burnley. On 1 December 2012, Grayson managed Huddersfield against his former side Leeds for the first time, losing 4–2 at home. He was dismissed by Huddersfield on 24 January 2013, following a run of 12 consecutive matches without victory stretching back to 17 November 2012.
Preston North End Simon Grayson was appointed manager of Preston North End on 18 February 2013 and went
unbeaten in his first four games in charge. Grayson then went on to keep the club clear of relegation with four games to go. Safety was confirmed after a 2–0 home win against Oldham Athletic on 9 April 2013. In May 2014 Grayson guided Preston North End into the League One play off semi-final against Rotherham United. However, after drawing the first leg at Deepdale 1–1, North End lost the return leg 3–1 despite taking an early lead through Paul Gallagher. Twelve months later, Grayson guided Preston back to the second tier of English football after being absent for four years with a victory over Swindon Town in the League One play-off final. It was their first success in the play-offs in 10 attempts and was notable for
Jermaine Beckford's three goals, becoming only the third player to ever score a play-off final hat-trick at Wembley.
Sunderland On 29 June 2017, Grayson was named as the new manager of newly relegated Championship club
Sunderland, replacing
David Moyes, on a three-year contract. His first league game as manager came on 4 August 2017, where his side drew 1–1 at the
Stadium of Light against
Derby County. In his following fixture, his team defeated
Norwich City at
Carrow Road, with the final result 3–1, Sunderland went on to record another draw, before commencing a four-game losing streak, until drawing one again. After a 2–1 defeat to
Cardiff City, Sunderland dropped into relegation zone. On 26 September 2017, his team suffered a 5–2 loss to
Ipswich Town at
Portman Road, with them moving down to twenty-third place in their division. Grayson's team then recorded three consecutive draws; however, they did not move from their league position. He was dismissed after a 3–3 home draw with
Bolton Wanderers on 31 October.
Bradford City On 11 February 2018, Grayson was announced as the manager of League One club Bradford City, following the dismissal of
Stuart McCall. He won three out of 14 games as they finished 11th, and left at the end of his contract in May.
Return to Blackpool On 6 July 2019, the day after
Terry McPhillips announced his resignation, Grayson was appointed Blackpool manager on a two-year contract. He was sacked on 12 February 2020, after a spell of four points from a possible 27 brought them from 4th place to 15th in League One. He managed
Kendal Town for one game in October 2020, covering for the self-isolating
Chris Humphrey.
Fleetwood Town On 31 January 2021, Grayson was appointed manager of
Fleetwood Town, following the departure of previous manager
Joey Barton. Grayson left Fleetwood on 24 November 2021.
Bengaluru On 8 June 2022,
Indian Super League side
Bengaluru announced the appointment of Grayson on a two-year deal. He reached the
2022–23 ISL Final with Bengaluru but lost on penalties to
ATK Mohun Bagan. On 9 December 2023, he mutually agreed to part ways with the club after a 4–0 defeat to
Mumbai City.
Lalitpur City Grayson was appointed head coach of
Nepal Super League club
Lalitpur City on 2 February 2025. He led the team to their second-consecutive
Nepal Super League title on 26 April 2025.
Hartlepool United On 12 June 2025, Grayson was appointed head coach of
National League club
Hartlepool United. Grayson had been a target for owner
Raj Singh for the vacant manager job at Hartlepool on previous occasions. He was appointed amidst uncertainty surrounding the future ownership of the club. Hartlepool saw a significant turnover of players during pre-season with Grayson handing debuts to eight new signings for the first match of the season, a 0–0 draw at
Yeovil Town. Hartlepool took 10 points from their opening four matches under Grayson. However, after a run of one win in 11 games in all competitions, Grayson was dismissed on 12 October following a 1–1 away draw with seventh tier side
Gainsborough Trinity in the
FA Cup fourth qualifying round. He departed after 14 league games with four wins, six draws and four defeats and with the club in 12th position in the National League. ==Personal life==