Real Madrid may have missed out on Manchester United goalkeeper David De Gea by as little as one minute, one report claims.
The move is widely reported to have broken down because the documents were sent after the midnight Spanish time deadline.
Bernabeu Digital add that United were late getting the paperwork to the offices of the Spanish League, the LFP, and Madrid were ready to announce the signing.
The report adds that the documents were one minute past the midnight cut-off and the LFP refuse to allow the deal to go through as a result.