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On 2 February 2018, Oyston rescinded his role as chairman of the football club.

On 2 February 2018, Oyston again resigned from his role as chairman of the football club after an alleged rift with his father.

On 6 November 2017, Karl and his father Owen Oyston was found in a High Court judgement to have operated an "illegitimate stripping" of Blackpool F.C., paying £26.77 million out of the club to companies they owned. The Oystons decided to put the club up for sale following the judgement.

On 6 November 2017, in a high court judgement, Karl and his father Owen Oyston was found to have operated an "illegitimate stripping" of Blackpool F.C., paying £26.77 million out of the club to companies they owned. They were ordered to pay £31m for the share of the minority shareholder Valeri Belokon, who invested £4.5 million for a 20% stake in Blackpool in 2006 and challenged the legitimacy of the payment the Oystons made to their own companies in the high court. Following the judgement, on 10 November, the Oystons decided to put the club up for sale.

In May 2016, Oyston won £30,000 in libel damages from Blackpool supporter Stephen Reed.

On 30 January 2015, another Blackpool fan, Stephen Sharpe, agreed to make a £5,000 donation to the club's Community Trust in lieu of damages and legal costs after posting defamatory messages about the Oystons on a website forum the previous year.

In early February 2015, the Oystons confirmed they were seeking another £150,000 in damages from Paul Crashley, the owner of the website Back Henry Street, over "six allegedly defamatory comments made in 2014". This action was subsequently lost after it was struck out by the court in December 2016.

In April 2015, the Oystons sued a third fan for libelling them on Facebook. Frank Knight, a 67-year old retired businessman later apologised on his Facebook page: “I now regret making these allegations, I fully accept that they are false and I wish to sincerely apologise for them." After Knight had agreed to pay £20,000 damages, the television personalities Russell Brand and Rachel Riley led a public appeal, raising £20,915 to cover the damages. The club issued a statement shortly thereafter, warning of further legal action against people who, they claim, make false statements against them.

In 2015, the Oystons also took action against Tim Fielding, the former chair of Blackpool Supporters Trust. Fielding resigned his position after the Oystons took exception to comments he made on fan websites and social media. He referred to the family as having "asset stripped" the club; as having "misappropriated football generated funds"; and as having made large personal profits by buying assets from the club at one price and then selling the same assets back to the club at a substantially increased price. "I now regret the allegations and unreservedly withdraw [them]." The claim about asset buying and selling was also made by the Daily Mail in 2014, but no action was taken against the newspaper.

Oyston has had a poor relationship with Blackpool's fans, mostly since the club's relegation from the Premier League, due to a perceived lack of funding for the club's stadium, playing staff and training ground. The relationship was described as being "at breaking point" by Tim Fielding, the chair of the Blackpool Supporters Trust, in December 2014.

In April 2014, with Blackpool flirting with relegation to the third tier for the second consecutive season, Oyston called for the police to investigate death threats aimed at him and his family. Fans had begun protesting at games, calling for Oyston to leave the club after failing to provide the necessary funding for the club's infrastructure, despite the club having received an estimated £80 million cash windfall after their victory over Cardiff City at Wembley. To compound the ill-feeling, Oyston paid his father £11 million, distributed another £26 million around other Oyston-owned companies, and purchased land owned by the club behind the stadium for £650,000, which was then sold back to the club for £6.5 million after a lease for a Travelodge had been secured.

Oyston's penchant for signing players via the loan market or on free transfers instead of paying transfer fees was highlighted during the 2014–15 season, before which 27 players had departed.

In July 2014, Channel 4 News aired an investigation into the club's finances. In it, forensic accountant John Frenkel states: "It has the appearance that the club is being run purely for the benefit of Mr Oyston”.

In December 2014, after Blackpool, then bottom of The Championship, lost 6–1 at home to Bournemouth, Oyston made headlines for allegedly calling one of the club's supporters, among other denigrations, a "retard" in a text message, one of a number released by the Tangerine Knights protest group. The following day, the Blackpool Gazette decided to scrap Oyston's weekly column "given such disgusting and offensive comments". Oyston issued an apology later that day, via the club's website, but club president Valeri Belokon called for Oyston to quit on the back of the incident. Three months later, Oyston was charged with misconduct by the FA. His appeal against the FA ruling was rejected on 1 June, and he was banned from all footballing activities for six weeks and fined £40,000.

Blackpool remained in the top tier for one campaign, and after failing to return from the Championship at the first attempt, they have finished no higher than 15th, with Oyston employing four different managers since 2013. In 2015, Blackpool were relegated to the third tier for the first time since 2007. The following season saw a second-successive relegation, to the bottom tier of English professional football for the first time in fifteen years.

In 2012, Oyston was fined more than £40,000 for illegally dumping waste from the building of the new stand. Hundreds of tonnes of rubble were found at Whyndyke Farm, despite there not being a permit to do so. Oyston pleaded guilty to two breaches of laws made to protect the environment.

During the 2012–13 season, the state of the Bloomfield Road pitch was criticised by managers and players. It was re-laid during the following close season, but in December 2014 it began to deteriorate again. In February 2015, the Football League contacted the club, demanding an explanation for the current condition of the pitch. The pitch was relaid during the summer of 2015.

On 18 August, he stood down as both chairman and director of the club with immediate effect, although he remained as Acting Chief Executive. It was subsequently reported that he had been made bankrupt on that date, which would have prevented him acting as chairman due to Premiership rules. The bankruptcy order was annulled on 12 October. Oyston returned to his role as chairman in 2011.

On 19 February 2011, Oyston married his partner, Victoria, at Christ Church in Over Wyresdale, near Lancaster. He has two sons, George and Sam.

On 26 January 2010, Oyston was elected to the Football League board of directors as a representative of the Championship in a ballot for the vacant position, but had to leave this post at the end of the season following Blackpool's promotion to the Premier League.

In August 2010, Oyston offered to stand down as chairman of the club, stating his belief that he has a different approach to the rest of the Premier League chairmen and the difficulties of dealing with top-flight players and their agents. Oyston said: "The more I speak to other people at other clubs, the more I realise I am a lone voice. There was some support for things I did and said in the Championship but there doesn't seem to be any in this division ... We are the ones who are the employers. We are the ones offering the terms and the contracts. It is up to us how we go about things. I don't think any deal should be about the agent. It should be about the player, and about giving the player a platform under a wonderful manager to perform on one of the best footballing stages in the world. Agents are sometimes denying their clients that chance."

In August 2010, nearly three months after their promotion to the Premier League, Blackpool's players received their bonuses, reported to be £400,000 each. Charlie Adam took Karl Oyston to court that October over a £20,000 short-payment on his bonus.

In September 2006, after an undercover investigation into illicit payments in football on the BBC Panorama current affairs documentary series, Oyston claimed that he had been offered bungs by football agents, saying "I've been offered cash as a bribe to bring a player to the club and it's happened more than once. In one instance, someone wanted me to take a player on a higher salary than we would normally pay, so he offered me a certain amount of cash as a gift to get me to do it. I said no and it didn't take any time whatsoever to reach that decision. Since 1999 when I became chairman here, my managers have been offered bungs. We've missed out on a lot of footballers because of it and that is one of my biggest concerns. It is very disturbing and in the Premiership where there are huge, huge deals taking place, it is a major problem." The Football Association asked Oyston, and others who made similar claims, to name the agents concerned, saying that they had a duty to provide evidence.

In July 2005, Oyston was elected onto the Football League board of directors as a representative of League One, and in June 2006 was elected back onto the board.

Bloomfield Road's South Stand was demolished in 2003. On 14 January of that year, Karl Oyston promised the redevelopment of the stand would go ahead but insisted he would not be pressured into making any rash decisions. Five years later, after no sign of building work became a source of controversy, Oyston stated: "The South will be built as and when it is right for the football business. I know we need to progress as a club and it is top of our agenda, believe me, but it wasn't right to do it now." He also confirmed that the club had no immediate plans to start building the stand. The stand was officially opened in March 2010.

At the time of Oyston's appointment, Blackpool were in the third tier of the Football League. At the end of the following 1999–2000 campaign, they were relegated to the bottom tier. At the first time of asking, they returned to the Second Division, where they remained for the next six seasons. In 2007 they were promoted to the second tier. Three years later, after financial backing from new club president Valērijs Belokoņs, Blackpool were, for the first time, promoted to the Premier League. After this promotion, Belokoņs was frozen out of day-to-day involvement, he claims because the Oystons no longer needed his financial backing.

Until 1999, Oyston spent much of his time involved in running the Oyston family businesses, including property management, farming interests and publishing.

On 3 April 1999, Oyston took over as chairman of Blackpool, becoming the third member of the Oyston family to occupy the role, after his father and mother, Vicki, from whom he inherited the role. Initially he took over the role of managing director, following the resignation of both the previous managing director, Gill Bridge, and Vicki Oyston, who had resigned as chairman following what was described as "an ugly 'Oyston Out' demonstration by fans at the stadium". Oyston had been handed control of the club by his father, who was, at the time, still serving a prison sentence for rape. Oyston stated that his mother had quit to give him a level playing field and let him run the club his way after his father had promised he would not seek to take over again upon his release.

Karl Samuel Oyston (born 20 February 1968) is an English businessman and the former chairman of Blackpool Football Club. Oyston took over the chairmanship at Blackpool from his mother, Vicki Oyston, in 1999. Mrs Oyston had taken over three years earlier when her husband Owen, Karl's father, was jailed for six years in 1996 for rape and indecent assault. In 2014, the Sunday Times Rich List listed the Oystons' wealth at £100 million, making them the 863rd-richest in the country at the time, down from 759th in 2008.