Liverpool have failed in a deadline-day bid to sign Fulham teenager Fabio Carvalho.
The Reds had agreed a £8 million ($11m) fee for the 19-year-old on Monday evening, and were prepared to allow him to remain at Craven Cottage until the end of the season.
But despite a day of negotiations, the clubs were unable to complete the necessary paperwork in time for the 11pm GMT deadline.
Why did the deal fall through?
Carvalho had looked Anfield-bound when, after lengthy negotiations, a deal was struck between the clubs on deadline day.
A medical was hastily-arranged in London, and a five-year contract prepared.
But with Fulham insisting on a loan-back arrangement, Liverpool were unable to finalise all of the necessary paperwork.
The EFL, unlike the Premier League, does not permit ‘deal sheets’ which would allow work to be continued after the deadline has passed, and Carvalho will now see out the remainder of his contract with the Cottagers.
Will Liverpool sign Carvalho in the next transfer window?
It remains to be seen whether Liverpool will return for him in the summer.
The Reds expect fierce competition to sign the England Under 18 international, which, along with their desire to avoid a lengthy compensation tribunal, was why they were keen to sign him this month.
It is understood that the likes of Bayern Munich, Borussia Dortmund and Chelsea are among those interested, and Carvalho would be able to move to an overseas club for just a nominal compensation fee.
Liverpool are, however, expected to try and finalise a deal in the coming weeks, with Jurgen Klopp and his recruitment team believing he is a player of significant potential who would develop well on Merseyside.
The Reds have, at least, made one significant signing in January, landing Colombia star Luis Diaz from Porto in a £50m ($67.5m) deal.
Meanwhile, Nat Phillips joined Bournemouth on loan on deadline day, while potential moves for Divock Origi and Takumi Minamino failed to materialise.
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