Rafael Benitez feels Liverpool have missed out on the chance to sign Milan defender Kakha Kaladze.
The Reds boss is expected to strengthen his defence in the New Year and Kaladze had been a top target.
But Benitez has suggested that he will no longer be able to bring the Georgian to Anfield when the transfer window reopens.
"I don't think we will be able to sign Kaladze now," said Benitez in the News of the World. "That opportunity has passed."
Instead, reports claim Benitez will look to push through the signing of Czech Republic international Tomas Ujfalusi from Fiorentina.
Ujfalusi is out of contract at the end of the season and his agent has admitted it is '50-50' regarding his chances of staying in Serie A.
Liverpool's interest in the centre-half has been confirmed and he could head to the Premier League in a cut-price deal in the New Year.