Dele Alli's agent has put his company into administration after being hit with a tax bill of more than £2million.

And documents filed with Companies House list Karl Robinson — the manager who was in charge at MK Dons when Alli was sold to Tottenham in February 2015 — among shareholders, along with former players Paul Robinson, David Bentley and Stephen Carr.

The agent Rob Segal is listed as director and principal shareholder. The company he founded back in 2004 — Impact Sports Management (ISM) — stands to make millions for shareholders should Alli make a big-money move to one of Europe's richest clubs.

Dele Alli's agent has put his company Impact Sports Management into administration

Rob Segal is Alli's representative and is being sued for debts of more than £2million

Tottenham have insisted they have no intention of selling but in recent weeks the brilliant young England international has been linked with Barcelona, Real Madrid and Bayern Munich.

But on October 20, 2016, ISM went into administration, with a statement of administrator's proposals filed to Companies House last month and now seen by Sportsmail. The statement says that 'the company has been very successful over the years'.

Indeed, Segal is regarded as one of the most powerful agents in football. But the administrator's statement explains that ISM's 'fortunes have been affected after an inspection by HM Revenue and Customs over four years ago'.

'At this inspection HMRC looked into the company's finances in depth and declared that, as a result of some items of expenditure which they deemed to be personal, they were intending to raise assessments for historical tax periods which, together with penalties, would bring about an estimated tax liability of in excess of £2.146m.

Segal and shareholders would stand to make a significant amount of money if Alli moved clubs

'The director and his accountants vehemently disputed this, and have been fighting the issue for the last four years. However, a resolution has not been reached and, in late August 2016, HMRC passed the matter to the collector of taxes who proceeded to raise assessments which totalled £2,611,145.88, including interest and penalties.

'This was followed in September 2016 by threats of enforcement action if the debt was not paid.'

Karl Robinson, now manager at Charlton, is one of Segal's clients and is credited with helping develop Alli before he joined Spurs. It is unclear how Alli came to be represented by Segal.

The talented Tottenham youngster has developed into one of England's finest players

Alli's former manager Karl Robinson was named as one of the shareholders at ISM

Robinson, still only 36, played as a striker in the lower leagues before coaching at Liverpool's academy and Blackburn led to him being appointed the MK Dons boss in May 2010. It was a position he held until his dismissal on October 23 2016.

Born in Milton Keynes, Alli joined MK Dons when he was 11 and made his first-team debut under Robinson at 16 in November 2012.

Robinson had long tipped him as a future England star, even though he had to defend the club's decision to sell the precociously gifted midfielder to Spurs.

'Nobody can turn around for one moment and say we could have kept Dele Alli,' Robinson told the BBC's Look East in April 2016.

ISM have been in an ongoing dispute with HMRC over the tax bill for four years

Segal's accountant says ISM is a victim of the treasury's eagerness to collect tax

It was on February 2, 2015, that Alli signed for Spurs in a five-and-a-half-year deal with an initial fee of £5m, remaining at MK Dons on loan for the rest of that season.

An annual return filed by ISM to Companies House in January 2015 does not have Robinson listed as a shareholder. But in an annual return filed on July 7, 2015, he is listed as a shareholder.

There is no suggestion of any wrongdoing, neither does there appear to be any breach under FA regulations regarding 'restriction on conflict of interest', though the position is not totally clear.

HMRC announced that along with penalties and liabilities the tax bill amounts to £2.146m

The ruling states that 'a player, club, club official or manager shall not have any interest in the business of an intermediary or an intermediary's organisation'.

But it then states that it prohibits 'beneficial ownership of more than 5 per cent of any entity, firm or company through which the activities of the club or intermediary (as applicable) are conducted'.

Segal's accountant, Paul Marks, of PJ Marks and Co Ltd, said: 'Robert's company has been a victim of the Treasury's eagerness to collect tax without determining its correctness.'

A Charlton spokesperson said: 'Charlton Athletic don't have any player from Impact Sport Management on the club's books.'

An MK Dons spokesman said they had no knowledge of Robinson's involvement.

Robinson was unavailable.