Tottenham Hotspur saw two transfer targets slip through its grasp Thursday.
Tottenham's move for Hugo Lloris appears to be in jeopardy after the goalkeeper's parent club Lyon revealed it had failed to reach an agreement with Spurs over Lloris' transfer.
Spurs boss Andre Villas-Boas also said it would be "impossible" for Tottenham to sign Porto playmaker Joao Moutinho.
Lyon claims Tottenham agreed a deal with them for the transfer of the 25-year-old Lloris four days ago, but they now say that the Londoners have lowered their offer for the player.
"The proposals forwarded this evening by Tottenham are very different from the principle which had been agreed on August 26 and which had allowed to open the discussions between the player and the London club," a statement on Lyon's website read.
Moutinho was expected to be the focus of Spurs' attention on deadline day on Friday, but Tottenham appears unlikely to sign him because of a 40 million euro ($50 million) release clause in his contract.
"This volume of money is out of Tottenham's possibility," Villas-Boas said. "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."
Villas-Boas also appeared 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.