Sir Jim Ratcliffe warned Man United he was prepared to withdraw his offer to become minority owner if it was not approved before Christmas Day.
The Red Devils announced on December 24 that the Ineos chairman had agreed to buy a 25 per cent stake in the club in a deal that included investing £236.7million into their infrastructure.
But, US Securities and Exchange Commission (SEC) filings released on Wednesday have revealed Ratcliffe's patience had begun to wear thin shortly before an agreement was struck.
In the week before Christmas, Ratcliffe's company Trawlers Limited 'gave Manchester United a deadline of December 25, 2023 to accept its best and final proposal'.