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Tottenham were knocked out of the Champions League as they were comprehensively outclassed by Monaco at Stade Louis II.
Djibril Sidibe’s header early in the second half sparked a stunning sequence of three goals in just five minutes that saw Spurs’ Champions League hopes swiftly fade, recover and fade again.
Harry Kane’s penalty, awarded when Dele Alli was pulled back, put Spurs on level terms but, just 39 seconds later, Monaco had the ball in the net again through Thomas Lemar.
Victory takes Monaco through to the last 16 as deserved winners of Group E ahead of Bayer Leverkusen, who earlier drew 1-1 at CSKA Moscow.
Spurs, who have won just one of their five group matches, are three points behind Leverkusen with one game to play, against CSKA on 7 December, but cannot overhaul the German side because of an inferior head-to-head record.
Mauricio Pochettino’s side kicked off knowing a draw in the principality would be enough to keep their hopes alive, but Monaco were by far the better side and only a superb performance by goalkeeper Hugo Lloris spared the Premier League side further punishment.
Lloris saved a Radamel Falcao penalty in the first half, produced a truly world-class stop to keep out Kamil Glik’s thumping first-time effort from a free-kick, and thwarted Falcao a second time after the break.