Andre Villas-Boas appears to have given up his pursuit of Joao Moutinho, claiming it will be "impossible" for Tottenham to sign the Porto playmaker.
Spurs are renowned for their last-minute forays into the transfer market. Last season they snapped up Scott Parker on deadline day and the year before they made a sensational swoop for Rafael van der Vaart.
Moutinho was expected to be the focus of their attention on Friday's deadline day, but Tottenham appear unlikely to sign the 25-year-old due to a 40million euro (Â£31.7million) release clause in his contract. Villas-Boas told a press conference: "It's an impossible deal for the club."
He added: "You have to bear in mind that this is a player with a 40million euro release clause. This volume of money is out of Tottenham's possibility.
"Bearing in mind that this is a key player for club and country, you wouldn't say that you would get him at half the price and half the price is already bigger than Tottenham's record fee."
The Portuguese, who has added Jan Vertonghen, Gylfi Sigurdsson, Mousa Dembele and Emmanuel Adebayor this summer, also appears pessimistic about his chances of signing Brazil forward Willian from Shakhtar Donetsk for the same reason.
"We had initial contact with Shakhtar, (who) again (are) a club in a position with wealthy owners, (and are) not easy to deal with," Villas-Boas added. "We can't say that it's over but we have approached the club and at the moment it's a deal that doesn't seem to be happening."
A last-minute bid for both players cannot be ruled out given Daniel Levy's history of 11th-hour deals, but it is unclear whether Porto or Shakhtar will be willing to drop their asking price for the respective players.
Jermain Defoe is one man who will be staying at White Hart Lane as the 29-year-old signed a new three-year deal with the club. Of the players who could leave Spurs, Van der Vaart is the most high-profile.
Hamburg have bid around Â£8million for Van der Vaart but Villas-Boas has told the German club they must up their bid significantly if they are to re-sign a player they sold to Real Madrid in 2008. Villas-Boas said: "We have had interest from Hamburg, but an offer of that dimension is not something the player deserves."