Liverpool saw an official £10m bid for Southampton right-back Nathaniel Clyne rejected, reports The Telegraph.
The England international has been strongly tipped to move to Manchester United this summer with Louis van Gaal ready to spend upwards of £20m on bringing him to Old Trafford.
With the Red Devils yet to make a move, Liverpool manager Brendan Rodgers hoped to swoop in and secure a deal for the in-demand defender.
However, Liverpool's £10m offer fell well short of Southampton's valuation of Clyne and now the Anfield club are considering a second, bigger offer.
Clyne has just 12 months remaining on his contract at St Mary's and has been in negotiations with the Saints over extending that deal despite talk of interest from the Premier League's top six.
Liverpool have bought many of Southampton's rising stars in the past 12 months, bringing Dejan Lovren, Adam Lallana and Rickie Lambert to Anfield last summer for a combined fee of around £50m.
They would hope that their familiarity with Southampton officials would give them the edge over Manchester United in the race for Clyne, but their absence from next season's Champions League represents a significant challenge.
The big problem
Should Clyne leave St Mary's he would surely like to go to a club in Europe's top competition, which Manchester United will be.
Despite these challenges, Rodgers is confident of convincing Clyne to make the move to Anfield where he can join several of his former team-mates.
This confidence is not misplaced as it is believed that Manchester United are reconsidering their interest in the 24-year-old.
The same report claims that interest from Manchester United is starting to cool off with Van Gaal believed to be looking at other targets. One of those targets is almost certainly Barcelona star Dani Alves, who is set to leave the Nou Camp for free when his contract expires this month.
Alves would certainly command bigger wages than Clyne but would arrive at Old Trafford with vast experience in winning Europe's biggest prizes.
Is Nathaniel Clyne the right man for Liverpool or Manchester United?
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