• Player available after £18m move to Bayern fell through
• Spurs are offering £8m for the Holland midfielder

Tottenham Hotspur hope to discover tomorrow morning if a dramatic last-minute bid to buy the Holland midfielder Rafael van der Vaart from Real Madrid in an £8m deal will be approved by the Premier League.

Harry Redknapp, the Spurs manager, was unable to confirm if the requisite paperwork had reached Gloucester Place before the 6pm deadline. The Guardian understands that a late deluge of documentation for various deals arrived right on the time limit and officials are still working to establish if the Van der Vaart deal made it in time.

“We’re waiting to see if it’s all gone through and hopefully it has,” Redknapp said. “We’re just waiting for some clearance. The chairman [Daniel Levy] and the secretary are dealing with it so I’ve left it to them. There’s more nothing [more] I can do. I’m going to head off home now.”

After a relatively quiet transfer deadline day in which little business was done among the bigger clubs, Redknapp’s attempt, if successful, would represent a coup for Spurs. He explained why the bid had come so late in the day.

“I thought he was going to Bayern Munich yesterday for about £18m and suddenly he become an awful lot cheaper and the chairman came to me and said, ‘Look, he’s available for around about £8m’.

“I felt we’d already got a good squad, it wasn’t a case of really being desperate to get anyone in. It was only when he rung me around at about four o’clock and told me there was an opportunity here and did I want to do something? I said, ‘I don’t really want to spend your money but if you feel you want to have a go then, well, let’s push on and give it a crack and see if we can pull it off.”

Redknapp, whose Spurs team are in the Champions League group stages, is in no doubt that the 27-year-old would add depth to his squad.

“He’s a quality player, a Dutch international, a great footballer. For that sort of money we felt he was a top player and he’ll improve us, for sure, so we made the effort but whether we can pull it off or not I’m not sure now. It could happen; I wouldn’t like to say one way or another but we are hopeful it’ll go through. It was a last-minute job.

“When I came in this morning it wasn’t something we were looking to do. We’d brought a couple in: I got William Gallas and Sandro joined us this morning – he came training for the first time with us today so I wasn’t too concerned.”

Should the Van der Vaart move gain Premier League approval, the midfielder would become Redknapp’s second deadline-day signing after Spurs earlier sealed a loan deal for the Croatia goalkeeper Stipe Pletikosa from Spartak Moscow.

The 31-year-old, who has won 80 caps for his country and has played in two World Cups and one European Championship, was close to joining Tottenham last summer before an injury scuppered the transfer. However, he won a move this time after impressing during a trial.

Elsewhere, Robinho finally ended his turbulent spell at Manchester City by finalising a £18m move to Milan while the Ghana striker Asamoah Gyan signed for Sunderland from Rennes for a club record fee of £13m.

Tottenham HotspurTransfer windowReal MadridJamie Jacksonguardian.co.uk

• Worries for Tottenham as they crash 4-1 at home
• Strong Spurs team prove no match for Spaniards

Though these fixtures are all about sharpness not scorelines, with Champions League fixtures arriving soon Tottenham must hit the ground running this season and Harry Redknapp’s team did not fare well by either measure at White Hart Lane last night, succumbing 4-1 to Villarreal.

Redknapp named a strong line-up for the visit of the Spaniards, the first of a hat-trick of friendlies against European opposition designed to ready the club for their Champions League play-off next month. Fiorentina and Benfica follow before Spurs begin their Premier League campaign away at Manchester City on 14 August. This result, though, did not bode well.

“They’re a great side, I was very impressed with them,” said the Spurs manager. “We had a good squad out, but they were sharp. They were different class.”

Jermain Defoe started up front, with Michael Dawson and Aaron Lennon the others of England’s World Cup squad involved, while Heurelho Gomes played in goal having missed the club’s pre-season tour of the United States. Jermaine Jenas, his influence at White Hart Lane surely threatened by Redknapp’s interest in Scott Parker, started alongside Tom Huddlestone in midfield, while Robbie Keane, similarly under pressure given his manager’s interest in Craig Bellamy, took the captain’s armband. Jenas, though, hobbled off with a leg injury inside the first 20 minutes.

With Dawson and co needing to shake off the disappointment of England’s time in South Africa as well as their summer rust, Spurs could hardly have got off to a worse start. David Fuster and Santi Cazorla had already gone close by the time the visitors opened the scoring after 21 minutes. The impressive Cazorla found space 20 yards out and shaped to shoot, only to play a wonderfully disguised dinked pass through to Giuseppe Rossi. The former Manchester United striker, himself needing a confidence boost after Italy’s dismal World Cup campaign, made no mistake.

Though Spurs were undone by a moment of individual excellence for the first, a portion of blame could be attributed to the rusty Dawson for the second. The central defender failed to cut out Marcos Senna’s through-ball and Rossi, clean through, again slotted calmly past Gomes.

Redknapp’s seven half-time substitutions, rather than disrupt Spurs’ rhythm – there was little to speak of anyway – in fact offered the home side greater fluidity and control. Gareth Bale has begun pre-season in the same impressive manner in which he finished the last campaign and on 55 minutes Spurs pulled one back. Peter Crouch took advantage of defensive hesitancy to slip in Giovani dos Santos, and the Mexican chipped the ball confidently past Diego López in the Villarreal goal.

Rossi, though, completed his hat-trick with 20 minutes to go, his long-range drive deflecting off Vedran Corluka to make it 3-1, and Marco Ruben added a fourth with four minutes to play. The Yellow Submarines, despite finishing seventh in La Liga last season, will play in the Europa League this year, following Mallorca’s expulsion after going into administration. If they do not hit their straps when things really kick-off, Tottenham could still join them.

Tottenham HotspurVillarrealFriendliesJohn Ashdownguardian.co.uk