Tottenham crashed out of the Champions League as they were comprehensively outclassed by a rejuvenated Monaco side 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, 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.
Tottenham, 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.
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.
The Ligue 1 title hopefuls cut through Spurs with ease from the outset, with full-backs Sidibe and Benjamin Mendy a constant menace.
Spurs defender Kevin Wimmer had a night to forget, but it was centre-back partner Eric Dier at fault for Monaco’s first-half penalty, lunging in clumsily on Fabinho. Falcao took the spot-kick, but his effort was tame and Lloris saved.
The French goalkeeper also made a double save from Mendy and Valere Germain but had no chance with Monaco’s opener, the hosts again working the ball with ease to the left flank, from where Mendy crossed for the unmarked Sidibe to head in.
Kane’s penalty four minutes later was the England striker’s first Champions League goal, but Spurs’ defensive frailties were again exposed straight from kick-off.
Monaco required just four passes as they worked the ball seamlessly into the area, where Lemar drilled low past Lloris.
Only a quite incredible save from Lloris to keep out Kamil Glik’s thunderous strike kept Monaco within touching distance, but a third goal – or indeed a fourth – would not have flattered Leonardo Jardim’s hosts.
Gambles backfire as Spurs pay price for home woes
Spurs’ early exit from the Champions League owes much to their struggles at their temporary Wembley home.
Back-to-back defeats by Monaco and Leverkusen left them with no margin for error heading into this game, which made for a difficult team selection with a vital Premier League match at Chelsea to come this weekend.
Mauricio Pochettino decided to rest key defenders Jan Vertonghen and Kyle Walker in favour of Wimmer and Kieran Trippier but the decision backfired, with Tottenham’s backline appearing disjointed throughout and Wimmer in particular off the pace and at fault for the first goal.
Spurs have one more match to come at the national stadium, but it will be far from the occasion they envisioned at the start of the campaign.
Instead of looking to book their place in the last 16 of the Champions League, they will host CSKA with only third place in the group and Europa League football up for grabs.