The Newcastle United owner is no stranger to controversy, as he has become more and more opposed by fans of the Premier League outfit because of his lack of investment in the squad.
However, for a chancge it is not Newcastle United with whom Ashley has a dispute, but Rangers in the Scottish Premiership.
The dispute surrounds an agreement between Ashley's sportswear company, Sports Direct, and the club for exclusive merchandise sales.
With the deal about to expire, the club wanted to take their busiiness elsewhere, but the sports retailer felt they should have the chance to outbid other companies.
At the High Court in London, a judge will look in to claims that the club, managed by Steven Gerrard, entered in to a new deal before the current one with Sports Direct had expired, thus breaching the terms of their contract.