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'.
Widespread discussions had been held between February's initial offer for a controlling stake and the ultimate outcome.
Ratcliffe agreed to slight concessions after conversations between December 18 and 22 but 'was not prepared to accept any of other changes proposed by the non-affiliated directors'.
It led to an informal meeting of the board of directors on December 22 and a 'robust discussion regarding the feedback from the offeror'.
The board representatives noted Ratcliffe 'could decide to withdraw [the] proposal if the board of directors was not prepared to move forward by December 25, 2023'.
That transaction was subsequently agreed on December 24, bringing an end to a process that started in early June 2022.
United met representatives of investment bank Raine 'on several occasions to discuss potential strategic opportunities to enhance shareholder value and serve the best interests of the football club's fans'.
The club entered into 26 nondisclosure agreements and 19 were invited to the first round of bidding, including Ratcliffe and Sheikh Jassim.
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