Manchester United were battling to buy Marouane Fellaini and Ander Herrera in a combined spend of a minimum £55m late on Monday evening as the 11pm transfer deadline approached and David Moyes contemplated ending the summer transfer window having made no major signing.
As the £23.5m buyout clause for Everton's Fellaini ended on 31 July, United faced the ignominy of having to pay more than this after Moyes and Ed Woodward, the executive vice-chairman, decided to allow it to expire in the hope the midfielder could be bought for less.
With Fellaini handing in an official transfer request at Everton's training ground early on Monday evening and United trying to negotiate complicated Spanish tax laws regarding the €36m (£30.5m) buyout clause of Athletic Bilbao's Herrera, the strategy of Moyes and Woodward had come down to a frantic effort to strengthen the squad in the closing hours of the window.
United officials were reported as having gone to the offices of the Spanish Football Association to pay the clause, only to be turned away because of paperwork issues, with the suggestion being that Herrera himself had to sign the cheque.
As the deadline approached there was the option of an extra hour being allowed as this was an international transfer, if United, Athletic and Herrera all filled in a 'Deal Sheet', stating extenuating circumstances, which had to be completed between 9pm and 11pm and filed to the Premier League.
This would have to have shown the agreed fee and terms and indicate that only a minor hitch that would not affect these details was halting the transfer. Yet with Fifa's transfer-matching system having a midnight cut-off point, it was the absolute latest the deal could run to.
United's late move into action came after Woodward decided finally to discard the joint-bid approach for Fellaini and his team-mate Leighton Baines. This came after a last offer of £40m was turned down by Everton for the pair over the weekend.
A £15m bid from United on Monday for Baines was rejected – the fee was the same as in the joint price – and Fellaini appeared the more likely acquisition. Yet with Bill Kenwright, the Everton chairman, effectively valuing the midfielder at more than £25m, United's resolve to sign Fellaini was being severely tested as the fee was £1.5m more than the player's buyout clause.
Regarding Herrera, United had decided initially to offer €30m despite knowing that, as Athletic field only Basque players, they would not be minded to sell unless forced to do so by the full €36m being bid to trigger the 23-year-old's release clause.
In last summer's prospective moves of Javi Martínez to Bayern Munich and Fernando Llorente to Juventus, Athletic had shown their determination to retain each player. In Martínez's case the €40m buyout clause had to be paid by the German club. For Juventus, who were not minded to pay Llorente's €35m clause, they had to wait until his contract expired.
United face the further complication of potentially having to pay, because of the hostile triggering of Herrera's clause, an extra 21% in VAT, or 50% tax on the €36m price.