A firm being investigated over "missing millions" meant to revamp Northampton Town's ground spent £36,000 on tickets and hospitality for a Premier League football club, the BBC can reveal.
Accounts for 1st Land Ltd, run by Howard Grossman, show the money was paid to Tottenham Hotspur.
The police are investigating the firm over "alleged financial irregularities" over the £10.25m for the revamp.
A spokesman for Mr Grossman said he did not wish to comment.
Northampton Borough Council loaned Northampton Town £10.25m to redevelop the East stand at Sixfields but the work was never completed.
Much of the money was passed on to the developers, 1st Land Ltd.
There is no evidence money from the council's loan (agreed in September 2013) ended up being spent on the Spurs tickets and hospitality, as 1st Land Ltd did receive a fraction of its financing from another source.
A BBC investigation into 1st Land Ltd has found the company director Howard Grossman and members of his family flew on a private VIP jet with members of the Tottenham Hotspur first team to watch a European match in Portugal in March 2014.
'Fly with VIPs'
The bank accounts indicate three payments were made between November 2013 and June 2014 to Tottenham Hotspur Football Club of £4,320 for tickets, and other payments to the club for £31,140, and £588.
The top price corporate hospitality at Spurs currently costs £26,000. It includes tickets and access to "fly with the VIPs".
Mr Grossman, director of 1st Land Ltd, and owner of the County Group, is pictured on social media at a European game at Benfica in 2014.
Also on the trip is son Hayden, a director in County Group companies, who is pictured on the VIP jet with one of the Spurs stars. It flew from Stansted's VIP terminal. Hayden Grossman also went on a VIP trip to Turkey in December 2014.
In a statement, Howard Grossman has previously said it would not be appropriate to comment "while official investigations are taking place".
In February, the BBC revealed claims made in court documents in an action between the football club and Howard Grossman and others, that millions of pounds of the loan money had been misappropriated. The claim was settled out of court.
The BBC later revealed how some of the money appeared to have been diverted to finance a string of unconnected planning applications by Mr Grossman and his associates.
At the time Mr Grossman said there was no evidence of misappropriation, describing the allegations as "outrageous and false".
Apart from the police investigation, two separate inquiries are looking into the way the borough council made the loan to Northampton Town Football Club.
A spokesman for Howard Grossman said: "We have no comment to make at this juncture. As we have made clear previously, our client is not prepared to have a 'trial by media' and at present it simply is not appropriate to respond to your further questions whilst official investigations are ongoing."
The BBC has been unable to contact Hayden Grossman.