He has also managed Queens Park Rangers (where he won promotion from Division Two in 2003–04), Plymouth Argyle, Leicester City, Blackpool, Crystal Palace and Millwall.

Holloway has a reputation amongst football fans for his West Country accent, off-the-wall interviews and amusing answers to questions from the media,[3] with a wide selection of quotes and soundbites being printed.

A native of Kingswood, near Bristol, Holloway grew up in Cadbury Heath, where his mother, Jean, lived in the same council house until her death in April 2018.

[citation needed] Holloway began his playing career as an apprentice with his hometown team Bristol Rovers, turning professional in March 1981 and making his league debut the same year.

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.

[7] 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 805-mile (1,296 km) round trip a drink.

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 3+1⁄2-year contract.

[13] 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.

[16] Winning just nine out of 32 games, Leicester were relegated from the Championship on 4 May 2008 entering for the first time ever in their, then one hundred and twenty four-year, history the third tier of English football.

[18] 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.

[22] 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".

[27] 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.

[33] 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 Philips in extra time.

[citation needed] 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.

[37] On 10 March 2015, following a 4–1 defeat at home to Norwich City, Holloway was sacked 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.

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.

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.

[46] 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.

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.

[52] 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.

[54] 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;[55] 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)."

[65] 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.

[66] In February 2023, Holloway applied for and was interviewed for the vacancy at Scottish Premiership side Motherwell, although the board eventually chose Stuart Kettlewell.

[71] Swindon's good form continued into 2025, thirteen points from six matches seeing Holloway named EFL League Two Manager of the Month for January 2025.

Holloway has learned sign language, and his quirky media-friendly quotes have made him a high-profile campaigner on deaf issues and concerns.

We're better people because of it.During the gap between leaving Leicester and his appointment as Blackpool manager, Holloway became involved with the self-sufficiency movement, acquiring a brood of chickens and learning sufficient carpentry to build what he described as "Orpington Manor".

He attended an educational event at Bloomfield Road in 2009 along with then Blackpool club captain Jason Euell, who had just recently been the victim of racist abuse.

[citation needed] Holloway cited, in an interview to BBC programme Football Focus, that part of his decision to move to Crystal Palace was to be closer to family following the expectation of his first grandchild.

[84] The podcast was put on hold whilst he spent time as the manager of Grimsby Town but following his departure he announced he was resuming his show and asked for questions to feature on his next broadcast by posting on his Twitter account.