Tottenham’s leading scorer Harry Kane won’t play again until March.
And with fellow attacker Heung-min Son, who is Spurs' second top goalscorer, set to join Korea at the Asian Cup in the next few weeks, coach Mauricio Pochettino could be facing a crisis.
England captain Kane, who is Tottenham’s top scorer with 20 goals in all competitions this season, hobbled away from Wembley on Sunday after picking up a knock towards the end of the 1-0 defeat by Manchester United.
In a statement, the club says: “Following preliminary assessments, we can confirm that Harry Kane has damaged ligaments in his left ankle.
“The striker will continue to be monitored by our medical staff as he commences rehabilitation and is expected to return to training in early March.”
Kane’s absence looks a major blow for Spurs, who are currently third in the league, with him set to miss an important period of the campaign.
The hitman will sit out the League Cup semifinal second leg against Chelsea at Stamford Bridge next week, which Tottenham are leading 1-0 thanks to his goal at Wembley in the first match.
He is also likely to miss both legs of the Champions League last-16 clash against Borussia Dortmund.
With eight-goal Son also out, it leaves Pochettino with Lucas Moura and Fernando Llorente to call upon up front, as the manager has already confirmed the club are not looking to sign players in the January transfer window.