Madrid - Manchester United's Spain goalkeeper David De Gea was facing an uncertain future on Tuesday after his expected move to Real Madrid was apparently scuppered when the paperwork did not arrive at the Spanish league on time.
As the clock ticked towards the midnight local time deadline on Monday, media reports said Real and United had reached a deal for De Gea to return to La Liga, with Real's Costa Rica keeper Keylor Navas going the other way.
However, when Spain's professional league (LaLiga) declared the transfer window shut there was still no official confirmation and reports later said that although De Gea had signed his new contract, the relevant documents had not arrived in time for him to be registered.
FIFA rules state that players can only be registered during one of two annual transfer periods, the other is in January, with the exception being if their contract has expired before the end of a registration period.
Sports daily AS quoted unidentified Spanish league sources as saying the paperwork had not been delivered until 28 minutes past midnight, while rival paper Marca reported that Real had proof the paperwork arrived at one minute before midnight and were still expecting the transfer to go through.
As things stand, however, De Gea, whose deal with United expires at the end of the season, could find himself out in the cold, at least until the end of the year.
As the transfer saga rumbled on, United coach Louis van Gaal left the 24-year-old former Atletico Madrid keeper out of the squad for the Premier League club's opening games of the season, with Argentina international Sergio Romero playing instead.
Real want De Gea as a long-term replacement for his Spain team mate Iker Casillas, the former club captain who joined Porto in July.
De Gea was selected last week for Spain's forthcoming Euro 2016 qualifiers against Slovakia and Macedonia although coach Vicente Del Bosque hinted he could lose his place in the squad if his club situation remained unresolved.