The Spanish goalkeeper David De Gea's transfer from Manchester United to Real Madrid has been scuppered because the relevant paperwork was not delivered to the Spanish professional league (La Liga) on time.
De Gea had signed his new contract with the Spanish club but the paperwork did not reach the league's offices before the transfer deadline.
Real's Costa Rica keeper Keylor Navas was due to sign for United as part of the deal but will now stay in the Spanish capital, they added.
No official announcement has yet been made by either club.
There is no precedent for Spanish clubs being given additional time to conclude transfers as there is in England.
Meanwhile the Manchester United striker Javier Hernandez has joined the German club Bayer Leverkusen for 18 million dollars.
The Mexico international was on the bench for Sunday's 2-1 defeat at Swansea City but has not started a Premier League match for a year. He has signed a three-year contract.
Hernandez scored 59 goals in 156 appearances for United after joining from hometown club Chivas de Guadalajara in 2010.
He spent most of last season on loan at Real Madrid.
Meanwhile, United's Belgian midfielder Adnan Januzaj has joined Borussia Dortmund on loan.
Goalkeeper Anders Lindegaard, 31, has signed a two-year deal with West Brom.
United are set to complete the 87 million dollar signing of 19-year-old Monaco forward Anthony Martial.
The striker, who has been linked with Arsenal, was allowed to leave the France squad today for a medical with Louis van Gaal's side.
Should he sign, Martial, who scored eight goals in 31 Ligue 1 games last season. will become the costliest teenager in football history.
He will also become Manchester United's third most expensive signing.
The Red Devils paid 144 million to Real Madrid for Argentina winger Angel Di Maria and 90 million to Chelsea for Spain midfielder Juan Mata.