Emre Can might have played his last game for Liverpool after being ruled out for the rest of the season with a back injury.
The midfielder is out of contract this summer and a number of clubs including Juventus have shown strong interest in the 24-year-old.
Can's involvement in the World Cup for Germany is also now in question as he faces a race against time to recover.
Jurgen Klopp had originally thought Can would be fit to face Manchester City in the second leg of the Champions League quarter-final but his condition has deteriorated.
The World Cup is now two months away and back injuries are notoriously difficult to remedy.
Can has featured regularly for Joachim Low's side and would have been likely to make it onto the plane for Russia.
In the meantime, his absence leaves Liverpool short of midfield options, particularly for Merseyside derby this weekend.
Jordan Henderson is suspended and Adam Lallana out injured again, with the deadly Mo Salah also nursing a tweaked groin from Wednesday night's 3-0 triumph over City.
No doubt Liverpool fans would love to see Can sign a new deal but the chances are looking increasingly slim and supporters may have seen him in a Reds shirt for the last time.
