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, grow and fade again.
Harry Kane’s penalty, awarded when Dele Alli was pulled back, put Spurs on level terms but, 39 seconds later, Monaco had the ball in the net again through Thomas Lemar.
Victory took Monaco through to the last 16 as deserved winners of Group E ahead of Bayer Leverkusen, who earlier drew 1-1 at CSKA Moscow.
Tottenham, who have won 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.
Spurs knew a draw 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 – who saved a penalty from Radamel Falcao – spared the Premier League side further punishment.