Bristol Rovers Holloway took over a club that was struggling both on and off the pitch. In his first season in charge of Rovers, he led the club to 17th place in Division Two (now League One). The next season, however, Bristol Rovers gained fifth place and made the
playoffs. Despite taking a first-leg advantage of 3–1 against Northampton Town, Rovers subsequently lost 3–0 in the second leg and went out 4–3 on aggregate in the semi-finals. The 1998–99 season ended with a somewhat disappointing 13th place. Holloway retired as a player following that season, having played more than 400 matches for Bristol Rovers, to concentrate fully on management. In 1999–2000, his last full season at the club, Rovers finished 7th, narrowly missing out on the play-offs.
Queens Park Rangers In February 2001, midway through the 2000–01 season, Holloway was appointed manager of QPR, where he was given the task of keeping the team in Division One. He failed to do so, as QPR finished second from bottom and were relegated to the third level for the first time in 34 years. Despite the relegation, Holloway stayed on and rebuilt the side. After steadying the ship in 2001–02, and a near miss in 2002–03, Holloway and QPR were promoted back to the second level in 2004, finishing second behind
Plymouth Argyle. Holloway's first full season in
The Championship ended with a respectable 11th place, and during the following season 2005–06, the club continued to hover around mid-table. Holloway was suspended (sent on gardening leave) as manager by Queens Park Rangers on 6 February 2006. The reason given by the QPR board was that the constant rumours linking Holloway to the vacant managerial position at
Leicester City were causing too many problems for the club. As it turned out, the Leicester job went to
Rob Kelly, and QPR went on to finish 21st, just one place above the relegation positions.
Plymouth Argyle On 28 June 2006, Holloway became the manager of
Plymouth Argyle, and promised to take the club to the
Premier League. On 12 August, after Plymouth beat
Sunderland away 2–3, in celebration of his first away win as manager, Holloway offered to buy every one of the 700 fans who made the round trip a drink. Following press speculation, on 21 November 2007, Holloway submitted his resignation to the Plymouth Argyle board, with speculation that he was about to be offered the vacant managerial position at
Leicester City. The Plymouth board issued a statement saying he was still employed by Plymouth and tied legally to his contract, and the board's decision on whether or not to accept his resignation would be made on Friday, 23 November. Having agreed a compensation package for his services, he was announced in a press conference by
Milan Mandarić as Leicester manager on 22 November, signing a -year contract. His departure, however, was met with negativity from Argyle fans. After an open top bus tour in Blackpool, after his Blackpool side won promotion to the
Premier League some three years later, Holloway said:
Leicester City Holloway made history when he became the first Leicester manager in over 50 years to win his first league game in charge, beating
Bristol City 2–0. On 7 February 2008, in a buildup to a match against Plymouth at the
Walkers Stadium, Argyle chairman
Paul Stapleton spoke negatively of Holloway for allowing several high-profile players to leave the club before joining Leicester. A total of five players left Plymouth in the January
transfer window, which he claimed was all Holloway's fault. Holloway, stunned by the claims, had his lawyers look at the statements, while Mandarić accused Stapleton of "
sour grapes" over Holloway's move to Leicester, saying Plymouth Argyle should be thankful for what he had achieved during his time there. Plymouth won the match 1–0 as Holloway's former charges came back to haunt him. Winning just nine out of 32 games, Leicester were relegated from the Championship on 4 May 2008 entering the third tier of English football for the first time in their history. On 23 May 2008, following the club's relegation, Holloway and Leicester City parted company by mutual consent. Reflecting on his time at Leicester, he said "Leicester City is a marvellous club and I am as devastated as anybody that this great club suffered relegation. I gave 100% to the cause but unfortunately we ran out of time. The fans here are a different class and deserve a lot, lot better. I'd like to wish everyone connected with Leicester City well for the future – the club will always remain close to my heart."
Blackpool manager in 2010 On 21 May 2009, it was reported that Holloway, after 364 days out of football, was set to be announced as the new manager of Blackpool following the departure of their
caretaker manager Tony Parkes. The appointment was confirmed later the same day with Holloway signing a one-year contract with the club. His first league game in charge of
the Seasiders was a 1–1 draw with his former club Queens Park Rangers at
Loftus Road on 8 August 2009, the opening day of the
2009–10 season. Nine months later, he guided the club to the
Premier League after winning the
play-offs following a sixth-placed finish in
The Championship, becoming only the second Blackpool manager (after
Les Shannon in 1970) to win promotion in his first full season. Holloway described the achievement as the best moment of his life, aside from seeing his children born. Holloway followed this up in late July by leading Blackpool to victory in the South West Challenge Cup annual pre-season tournament. It was the first time a Premier League club had taken part. Before the start of Blackpool's first top-flight season in 40 years, media reports suggested that Holloway was set to resign as manager following an alleged dispute with club chairman
Karl Oyston. However, at a
press conference held at
Bloomfield Road on 11 August to announce the arrival of four new players, Holloway swiftly denied the rumours, describing his relationship with Oyston as "absolutely fantastic". And adding: The following day it was reported that Holloway had signed a new two-year contract. On 27 January 2011, the Premier League fined Blackpool £25,000 for fielding what they believed to be a weakened team against
Aston Villa on 10 November 2010. Holloway, who initially threatened to resign if punishment was dealt, made ten changes to the team for the fixture. Holloway was made aware of the fine over the phone while playing
golf with his wife at Shawhill Golf Club in
Chorley. He offered his resignation to Karl Oyston, but it was rejected. On 22 May 2011, Blackpool lost their Premier League status after losing 4–2 to champions Manchester United at Old Trafford, coupled with results elsewhere, and returned to The Championship after one season. Holloway marked his century of games in charge of Blackpool with a victory, the 37th of his reign, over
Ipswich Town at Bloomfield Road on 10 September 2011. In May 2012, Holloway guided Blackpool into The Championship play-offs for the second time in as many seasons in the division. They lost 2–1 to
West Ham in the play-off final. Holloway's win percentage in League games as Blackpool manager was 37.8% (54 wins from 143 games).
Crystal Palace On 3 November 2012, Holloway agreed to join Crystal Palace as manager, although caretaker manager
Curtis Fleming remained in charge of the team for the match on that day. He took charge of his first game on 6 November, which Crystal Palace won 5–0 against
Ipswich Town. On 27 May 2013, Holloway guided Crystal Palace to
promotion to the 2013–14 Premier League after beating
Watford 1–0 through a penalty converted by
Kevin Phillips in extra time. In the
2013–14 Premier League season, Crystal Palace started with just three points from the first eight
games as Holloway came under pressure to keep his job. On 23 October 2013, after a 4–1 loss against Fulham, Holloway left the club by mutual consent after less than a year in charge.
Millwall On 7 January 2014, he signed a two-and-a-half-year contract with
Millwall. He then guided the club to Championship safety for the 2013–14 season as Millwall finished 19th, four points above the relegation places. In the 2014–15 season, as Millwall dropped in the relegation places in
The Championship, Holloway admitted that he had become an unpopular manager among Millwall fans. On 10 March 2015, following a 4–1 defeat at home to
Norwich City, Holloway was dismissed for the first time in his managerial career, with the team second from bottom in the Championship and having lost five of their last six games.
Return to Queens Park Rangers On 11 November 2016, Holloway was appointed as manager of
Queens Park Rangers on a two-and-a-half-year deal. He arrived at a team who were in 17th place after the dismissal of
Jimmy Floyd Hasselbaink. His team avoided relegation on the penultimate day of the season with a 2–0 home win over
Nottingham Forest. Holloway left QPR on 10 May 2018, amid speculation that
Steve McClaren was being lined up to succeed him. He had finished 16th in the recently concluded season, and was congratulated by chief executive Lee Hoos for achieving results while the club was cutting costs.
Grimsby Town On 29 December 2019, Holloway joined
Grimsby Town as manager. At the same time he became committed to becoming a shareholder in the club and confirmed he would be purchasing £100,000 of shares, thereby allowing him to attend board meetings in addition to his duties as club manager. Holloway was appointed as a director in the process. The Mariners won their first two games under him with a 1–0 win at home to
Salford City followed by a 1–0 win away at
Mansfield Town the following week. Holloway made a host of signings that included his former
Blackpool players
Billy Clarke and
Elliot Grandin. On 7 March 2020 the side played out their final game of the season with a 2–0 win away at local rivals
Scunthorpe United before the season was cut short and ended early due to the
COVID-19 pandemic. In February 2020, majority shareholder
John Fenty announced he was going to be taking a step back and allowing Holloway more freedom and autonomy to run the club both on and off the field. Holloway made wholesale changes to the Grimsby side over the summer which included seven loan signings, despite only having the ability to name five in a match day squad. On 22 November 2020, following a 5–0 defeat against
Tranmere Rovers, Holloway announced he had released one of his recent signings
Bilel Mohsni despite recently stating "he is my leader, he is my
Virgil van Dijk". Mohsni despite not playing in the 5–0 defeat was confirmed released as he did not meet Holloway's standards, this prompted Mohsni to set up a Twitter account and post a video to announce that he had not left the club, was still contracted, feeling fit and would be at training the next day. The following day, Holloway said that he thought the termination had been agreed and that it was not his concern whether the player remained at the club until January. Mohsni signed for
Barnet on 1 December 2020. On 17 December 2020, it was discovered by the
Grimsby Telegraph that John Fenty had entertained
Manchester-based convicted fraudster Alex May at a Grimsby Town game, with May looking to invest £1 million into the club. However, with the news of his offer on the table it was met with strong resistance by fans leading to the deal to be turned down by the club. Unrelated to the May offer, but during the same week the club had also confirmed it had met with a consortium of local businessmen fronted by London-based Tom Shutes about a potential takeover. Holloway hit out at the consortium by saying that he was finding it increasingly hard to do his job. He also announced he was backing away from his director duties to concentrate on his position as manager and would be using social media more often to communicate with supporters, claiming also that he would not be going anywhere unless told so. It was also announced that Holloway had not yet invested any money into the club like first thought, and that this investment would now only be made upon the sale of his house in
Bristol. Following Grimsby's 1–0 victory over Scunthorpe on 19 December 2020 he stated that he would not be going ahead with plans to invest any of his money in the club due to the on-going discussions in the boardroom and continuing talks of a takeover. On the morning of 23 December 2020, just hours after Grimsby's 1–2 home defeat to
Bradford City, Holloway resigned as manager. He had been in charge just under a year, leaving them 20th in
League Two with only five wins from nineteen games. His reason for departing was his displeasure at Fenty's decision to sell his shares in the club, claiming he did not want to carry on at the club without the people he came here to work with. Holloway also stated that a key factor in his departure was that the potential consortium interested in buying the club had reached out to him and contacted him several times and he found this to be inappropriate; although a statement later released by the potential investment group denied that any of them had ever had any contact with Holloway and stated "Several weeks ago, we did make it clear through a mutual friend that we were very supportive of Ian and that if we were to take over as custodians of the club we wanted to build a legacy with him in place (which we also communicated to Philip Day in our discussions over the last week)." The group also expressed surprise and disappointment at his resignation. Later that day Fenty officially rejected a potential takeover over bid from the consortium, although terms were finally agreed on 29 December 2020 to sell the club to
Jason Stockwood and Andrew Pettit, members of the Shutes consortium. Grimsby replaced Holloway temporarily with his assistant
Ben Davies who following the club's next game, commented "I had a good chat with him, and everything was okay. We went into the game against Bradford on Tuesday night, and he came in the next morning and said he'd resigned. Obviously it's hard to take when you get close to someone over the last year or so, but that's the way it goes." After his resignation, Holloway drew criticism in both the nature of his departure and the state and quality of the team that he had put together during the summer, with the squad he left behind bloated in numbers and lacking in quality. Holloway later stated that he had left the club in a better position than when he arrived, despite the club being embroiled in a relegation battle with a squad that seemed destined for relegation. On 12 January 2021, Grimsby Town became the first football club in England to be fined for breaking COVID-19 protocol after an
EFL investigation revealed that the club had broken several social distancing rules, including Holloway having played
darts with some of his players at the club's training ground. On 27 April 2021, Grimsby were relegated back to non-League for a second time. Former Mariners player and
BBC Humberside co-commentator
Gary Croft blamed Holloway for using the club as "a bit of a play thing", and reflected that "I just can't believe that people have stood around and watched it happen, watched it unfurl without getting into him, questioning him, and finding out what's going on".
Unemployed years Following his initial departure from Grimsby, Holloway went on to state that he was unsure whether he would return to football management again, saying his appetite for football had diminished. In a podcast interview in late 2022, Holloway blamed his Grimsby departure on the
COVID-19 pandemic and the fact that his scouting network was not suited to operate at League Two level. He also stated he would be interested in a return to management, but only at
EFL Championship level. In February 2023, Holloway applied for and was interviewed for the vacancy at
Scottish Premiership side
Motherwell, although the board eventually chose
Stuart Kettlewell.
Swindon Town On 25 October 2024, nearly four years since he left his last role, Holloway was appointed as manager of
EFL League Two club
Swindon Town, taking over with the club in 22nd place. Following Swindon's poor form, Holloway quipped that he believed Swindon's training ground was haunted. On 14 December 2024, following a 1–0 defeat to
Bradford City, Holloway had to be restrained by his players after an altercation with a Swindon supporter. Holloway, who had won only one of his opening seven games, angrily addressed the fan in a post-match interview and suggested that the supporter should not travel to away games anymore. On 21 December, Holloway defeated former club Grimsby Town in his 1000th managerial game, but again criticised supporters after the game who held a protest against the board, stating that it only represented a minority of fans. He also stated: "If you don't like me or the club or what we are doing then don't come, I believe that I will get thousands who will come." Swindon's form continued into 2025, with thirteen points from six matches seeing Holloway named
EFL League Two Manager of the Month for January 2025. In February 2025, Holloway was charged with misconduct by the EFL for abusive language towards a match official in the fixture against
Chesterfield on 22 February. Holloway had been sent from the touchline. On 28 March 2025, having earned 36 points from 24 matches, Holloway was rewarded with a new long-term contract to keep him with the club until June 2028. ==Personal life==