Liverpool have failed with a late bid to sign winger Yevhen Konoplyanka from Ukrainian Premier League side Dnipro.
Managing director Ian Ayre spent three days in Ukraine trying to negotiate a 15 million pound deal.
But Dnipro’s billionaire owner Ihor Kolomoyskyi refused to sanction the transfer even though Liverpool agreed terms with Konoplyanka, sources told ESPN.
The 24-year-old Ukraine international was keen to move to Anfield and underwent a medical in his homeland in a bid to speed the deal through.
Kolomoyskyi, though, would not sign the paperwork to allow one of his star players to leave the club, causing frustration for both Ayre and manager Brendan Rodgers.
It is the second time during the January transfer window that Liverpool have missed out on a major transfer target.
They had been in talks to sign Egyptian winger Mohamed Salah from Basel, but Chelsea nipped in to agree an 11 million pound fee and completed the deal last Sunday.
Rodgers had warned earlier on Friday that the deal for Konoplyanka was fraught with difficulty, suggesting that talks had been “complicated”.
But Rodgers claimed he was "very optimistic" about the group of players he has at his disposal, with the team on a high following their 4-0 thumping of Everton in the Merseyside derby.
Rodgers admitted January was an awkward time to add players, saying on liverpoolfc.com: "I think it's difficult in order to bring certain players in that are going to help us immediately. The availability of the player, and of course the affordability, are always the two factors involved in getting a player in.
"It certainly hasn't been because of a lack of work by the football club. There are lots of people who have worked tirelessly to identify and find the right types of players. A lot of those players haven't been able to become available for us.