More than 100 footballers including recently retired Premier League players are in severe financial difficulties and even face bankruptcy, due to demands from Her Majesty’s Revenue and Customs for repayment of huge disputed tax reliefs, the Guardian has learned. Some players who earned six-figure and million-pound-plus salaries during good careers in English football’s current boom time face losing everything.

Around 100 players, said to be in financial “dire straits”, are understood to have sought help from the players’ union, the Professional Footballers’ Association. Xpro, the welfare organisation for former players, is representing 40 more, according to its chief executive, Geoff Scott. He said all 40 are seriously affected by HMRC demands for the repayment of tax reliefs granted on various investment schemes, with around 20 facing potential bankruptcy and some even homelessness.

Scott said the players signed up to the schemes, which gave them large reductions in tax bills, because financial advisers targeted high-earning footballers and it became a culture within the game.

“Many entered into them because they saw their team-mates doing it,” Scott said. “They considered their job was on the pitch, and their advisers were looking after them off it. We are representing 40 players, many are divorced, houses are being repossessed, some guys have gone bankrupt already, and we know of 20 facing bankruptcy or an individual [insolvency] voluntary arrangement principally because of tax demands.”

The footballers, who include stars of the game and solid ex-professionals, have become targets for a crackdown by HMRC on what it sees as tax avoidance. HMRC has challenged a number of schemes that, it argues, took advantage of reliefs aimed at boosting investment in the British film industry. Two of the film schemes being disputed, which were set up and run by the London firm Ingenious Media, had around 70 former and current footballers signed up, including stellar names, which are publicly recorded at Companies House, such as Gary Lineker, David Beckham, Steven Gerrard and Wayne Rooney. Those stars are all thought to be wealthy enough to cover any HMRC demands but the investors also included lesser famed and earning players, some of whom are seriously struggling to pay.

One footballer who invested with Ingenious, and spoke to the Guardian on the condition of anonymity, said he had played for a Premier League club for several years. He said he signed up for the investment schemes when he was earning his Premier League salary, on the recommendation of financial advisers and because “everybody else was doing it”. He has received four large demands for tax repayment from HMRC and, only recently retired from football, is divorced, facing bankruptcy and needed the PFA to help provide him with somewhere to live.

At the time he signed up, the player said, financial advisers were attaching themselves to high-earning footballers, winning their trust and friendship, and were frequent visitors to training grounds. He acknowledged there was “a little bit of greed” about investing in a scheme that resulted in large tax reliefs but argues he did so quite casually, without fully understanding them, and said his advisers did not fully explain that HMRC could rule such a scheme invalid.

“I am in trouble; there is no way I can pay the sums being demanded,” he said. “It is a really difficult period for me. I wouldn’t say it cost me my marriage but the pressure contributed to it. Your career comes to a very abrupt end and now, if I don’t go bankrupt, I will be close to it.”

The player, who did not want to be named because he is concerned it will affect the low-level employment he has recently found in football, said that after divorcing and leaving the family home, he found himself in severe trouble and asked the PFA for help. Five or six former players at his old club are suffering similar financial wipeout from tax relief claw-back demands, he said.

“There are so many of us in trouble; with my ex-colleagues, we want to be talking about the good times, but this is the topic of conversation everywhere. I am not looking for sympathy, I blame myself for trusting advisers – and I do think something should be done about them – and probably for being greedy as well, making a few grand from the taxman.”

The footballers were among hundreds of wealthy investors who signed up in the early 2000s for similar investment schemes. The standard schemes gave a large upfront payment of public money, but it was effectively only deferring tax due in later years, and many investors found they did not have the money when the demands rolled in.

The Ingenious Media schemes, which the company is determinedly defending in the upper tax tribunal in the royal courts of justice, were different, operating more as standard investments in the British film industry. Large numbers of people, including the footballers, invested some of their own money which was often, although not always, matched by almost double the money in the form of a loan. The value of each film was written down substantially in the first year, on the basis that films are risky ventures, and this produced a tax relief at the then higher rate of tax, 40%, of that first-year loss. In a standard example, this tax relief was as much as the actual cash the investor had put in, and could be used to reduce tax owing on other investments.

Many of the people who were attracted into these schemes remained investors for several years.

It is not publicly recorded how much each individual investor paid into the schemes but the tax reliefs paid to a total of eight schemes, which included those of Ingenious Media, now being disputed by HMRC amount to £1bn. Scott said the former Premier League players whom Xpro is advising face a total £300m in repayment demands by HMRC, which he called “staggering, a shipwreck”.

The Ingenious Media film schemes were challenged by HMRC, which is demanding the tax reliefs be repaid, arguing that two schemes in which so many footballers invested, Ingenious Games LLP and Ingenious Film Partners 2 LLP, did not operate in a way that really qualified. The crucial question is whether the partnerships of investors can be said to have “carried on a trade”. HMRC argues the partnerships could not be said to have done so, while Ingenious is strenuously defending the schemes, arguing that they were genuine trading investments in some major films and the tax reliefs were validly accrued.

In an interim judgment in the dispute last year, Mr Justice Sales said of the case: “HMRC’s conclusions, after investigation of [the film schemes’] affairs, [were] that the appellant partnerships were not at the relevant times carrying on a trade.”

Sales said: “The tax in issue in the proceedings is said to be of the order of £1bn. On any view, this is major tax litigation.”

Ingenious is fighting the HMRC view, arguing that the partnerships were trading, produced major films that made profits subsequently, resulting in tax being paid, and that the accounting was properly done. In a statement the company said: “The film partnerships run by Ingenious Media have already generated over £1bn in taxable income for the UK treasury, with more to come over the lifetime of the films they funded. They helped to bring movies including Avatar, the Best Exotic Marigold Hotel, the Girl with a Pearl Earring, Vera Drake, Shaun of the Dead, Hot Fuzz and Hotel Rwanda to the screen and are clearly run for profit. As regards the Tribunal, the hearing is ongoing and Ingenious remains confident of the outcome.”

However, under powers introduced after the 2013 autumn budget statement, HMRC can now demand to be paid a disputed tax amount upfront, even while a case is being heard. This is a reflection of the sterner, post-banking collapse view of tax avoidance.

The power allows HMRC to issue a settlement offer to people involved in a tax dispute. Settlement offers, which expired on 31 October, are understood to have been made in the case of the film schemes and some players are said to have taken them up, with one, according to a source close to the dispute, paying £1.2m. Players whose careers are continuing, or those who have moved into lucrative media roles, are said to have been able to manage financially, and some have paid the settlement and moved on.

One player the Guardian spoke to, who did not want to be identified, said that he declined to settle and wants to wait for the outcome of the tribunal case, arguing that he did nothing wrong and the schemes’ tax reliefs were considered valid at the time he invested.

In guidance it gave to explain the new powers, HMRC was adamant that the system is fair, and is being applied to the wealthiest people in the country rather than the vast majority who pay their tax upfront, which is retained by HMRC if there is any dispute. The guidance stated that “accelerated payment notices” relating to tax avoidance cases would be issued to around 33,000 taxpayers, concerning £5.1bn under dispute. HMRC emphasised that the people affected had an average gross income of £262,000. “These measures will predominantly affect individuals with above average incomes,” HMRC said.

For many of the footballers who spent or invested the reliefs they received several years ago, it was a huge shock to receive sudden, massive demands for tax reliefs they were barely aware of having had, years ago. Some with understanding of their situations say that players’ money was being managed in a portfolio of investments, some of which did not come off, they all had expensive lifestyles, and many do not have the money now to repay HMRC.

None of the players registered at Companies House as investors in the Ingenious Media schemes wanted to talk to the Guardian about it, except the one who was prepared to do so anonymously. Some clubs that replied on behalf of current players said it was policy not to discuss personal affairs. The PFA chief executive, Gordon Taylor, declined to comment partly because the Ingenious tribunal case is still going on and because players’ investments are private matters.

“The rationale and motive for any investment is simply not known to us and we are mindful of making general comments which may be misconstrued,” Taylor said.Scott, who played for Stoke City and Leicester City in the 1970s and 80s, and has formed Xpro to address major problems he says players of all generations suffer after retirement, believes many who invested in these schemes were badly advised. He said that although modern players earn vastly more than his generation did, they spent a lot of money while they were playing and financial advisors made commissions by selling investments to them. Xpro, Scott said, is at an advanced stage in considering whether the players have a case for suing some of those who advised them to invest.

Martin Taylor, of the financial firm Rebus which advises people facing enormous tax demands on how to negotiate their way through them, said he has been inundated, including by footballers affected. “Most players were sold these schemes as a good investment and a way to save tax, then they have retired, their earnings have dropped, they face very big accelerated payment notices from HMRC which can’t be appealed, and they are in serious financial difficulties,” he said.

One agent to top players, who also did not want to be named, said he believed there had been a culture of seeking to minimise tax bills. He said that although the players earned salaries way beyond the realities of ordinary people, the consequent size of the tax bills leads richer people to resent paying tax more than the less well paid.

The footballers high-rolling on salaries of which their predecessors never dreamt were susceptible to schemes, apparently legal at the time, that could reduce their tax bills and earn some money as well. Now, massive bills from investments they entered into quite casually are dropping through their letter boxes and in many cases wiping out every penny of the glittering fortunes they earned.