Tottenham were knocked out of the Champions League with a group stage game still to play after a 2-1 defeat by Monaco on Tuesday.
Monaco, who had the better of the first half, saw a penalty from Radamel Falcao saved well by Hugo Lloris after Eric Dier had brought down Fabinho.
But they went ahead just after the break as Dijbril Sidibe headed past Lloris from six yards after Benjamin Mendy's cross. Harry Kane levelled from the penalty spot after Dele Alli was hauled down by Kamil Glik.
Barely 40 seconds after Spurs had levelled, Monaco made it 2-1 through Thomas Lemar, who fired into the bottom right corner of the goal in acres of space inside the area.
The result means Spurs cannot reach the last-16 due to Bayer Leverkusen's superior head-to-head record against them, and must avoid defeat against CSKA Moscow at Wembley in a fortnight's time to secure a Europa League knockout stage spot.
Harry Kane drew Spurs level from the penalty spot
After Leverkusen were held 1-1 by CSKA in the early game in Group E, Spurs kicked off knowing a draw would be enough to take it to the sixth and final matchday.
Mauricio Pochettino made three changes after the 3-2 win over West Ham, bringing in Kieran Trippier, Heung-min Son and Kevin Wimmer.
They should have been ahead early on after Dele Alli played Son through on goal, but the South Korean fluffed his chance as he tried to take the ball around Monaco goalkeeper Danijel Subasic.
Hugo Lloris saved a first-half penalty from Radamel Falcao
The Ligue 1 side were awarded a penalty with 10 minutes gone after some lax Spurs defending resulted in Fabinho being caught by Dier's stray leg, but Falcao saw his spot-kick saved superbly by Lloris down low to his right.
Lloris then recovered well again after parrying Benjamin Mendy's effort from the left angle into a dangerous area, before Valere Germain's free header at the far post hit the chest of Wimmer.
Germain, who caused problems throughout for Spurs with his running in behind the defence, then flashed a shot from an acute angle just wide of Lloris' right post, and Spurs were lucky to go into the break unscathed.
Dele Alli reacts to a foul in the first half
Monaco finally took the lead after the break, Sidibe's powerful header getting past Lloris after Mendy's dangerous cross from the left.
Spurs went up the other end moments later and were level after Alli's fine turn forced Glik to bring him down, Kane converting for his fourth goal in three games since returning from injury.
Merely 40 seconds later, Monaco went ahead again through Lemar, who found the bottom right corner of Lloris' goal after being found in acres of space by Sidibe.
Lloris kept the visitors in the game in the final stages, producing a world-class save from Glik's close-range effort from a cross, before parrying away Falcao's well-hit shot inside the area.
Tottenham's goalkeeper Hugo Lloris put in a fine performance
Alli missed a late chance at the far post from Christian Eriksen's corner, turning the ball wide on the stretch, and Monaco held on for the win to send Tottenham out of the Champions League in Pochettino's first season in the competition.
The win also continued Monaco's fine run against English sides in the competition, having knocked out Arsenal, Chelsea and Manchester United over the past 20 years.
Paul Walsh's view on Soccer Special
"I think they will go for it in the Europa League, it's a route back into the Champions League.
"The way they're playing at the moment, the wheels of their season could come off, and there's no guarantee they'll finish in the top four, so they need every route open to them. They've got to stop dreaming and start playing again.
"I can't describe their Champions League form. After that fantastic result against Manchester City, I just don't really know what's gone wrong.
"The fluency, belief, confidence, seems to have drained out of them, and especially in the Champions League they've been so poor. They haven't had a performance in any of their five games."
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