Sky Sports News understands Tottenham Hotspur missed the deadline to finalise the paperwork for the signing of Rafael van der Vaart.
Spurs made a late bid to bring in Holland international Van der Vaart and tried to complete the deal before Tuesday's 6pm cut-off.
However, it is understood that technical issues prevented the necessary paperwork from being completed and Spurs have now requested special dispensation from the Premier League to add the midfielder to their squad.
The club were not initially expected to be particularly active on deadline day, but the sudden availability of Van der Vaart at a knock-down price of £8million prompted Spurs to act.
Manager Harry Redknapp told Sky Sports News on Tuesday evening that he was hopeful of signing Van der Vaart and conceded the club could not pass up such an opportunity.
"I think he was going to Bayern Munich yesterday for about £18million, but suddenly it became an awful lot cheaper," said Redknapp.
"He is available now for about £8million. He is a quality player. He is a Dutch international and a great footballer.
"For that sort of money, he is a top player and he will improve us for sure. We have made the effort, whether we can pull it off or not we will have to see.
"I am hopeful. It could happen. It was a last-minute job. When I came in this morning it certainly wasn't something I was looking to do."
He added: "He is a great passer of the ball, he is a top footballer. He will join in here and play the way we like to play, he would be a big plus for us.
"He looked like he was going for £18million but then the fee came crashing down because the deadline got close. If the chairman can pull it off, I think he will have got a real bargain."