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Harry Kane suffered a potential season-ending injury as Tottenham were left to count the cost of a stunning Champions League win over Manchester City.
Son Heung-min struck late on as Spurs claimed a first-leg advantage in the all-Premier League quarter-final with a 1-0 victory at the Tottenham Hotspur Stadium.
But the gloss was taken off the success by fears their talisman Kane, the England captain, could face another lengthy lay-off with an ankle injury.
Kane rolled the joint as he challenged Fabian Delph for the ball just before the hour. To compound matters, Delph then caught him on the ankle.
Kane, who was out for more than a month after suffering ankle ligament damage in January, was carried straight down the tunnel and later left the stadium on crutches wearing a protective boot.
"It is so painful," said manager Mauricio Pochettino. "We hope it is not a big issue and try to recover as soon as possible but it doesn't look good."
Asked if he was worried Kane's season could be over, Pochettino said: "Yes."