Tottenham Hotspur's Champions League campaign has come to an end after they were beaten 2-1 by AS Monaco at the Stade Louis II on Tuesday night.
Mauricio Pochettino's side are no longer able to mathematically qualify for the last-16 stage, despite having one final game against CSKA Moscow left in Group E.
Harry Kane was able to slot home from the penalty spot just three minutes after Djibril Sidibe put Monaco ahead in the second half, but 38 seconds later, Thomas Lemar nabbed the winner for the home side.
Son Heung-min was gifted a goalscoring opportunity in the sixth minute when Monaco's high line let go of the ball, allowing Dele Alli to play in the South Korean.
After getting one on one with goalkeeper Danijel Subasic, Son tried to work his way around him in the box, but he ended up being forced out wide and the move broke down.
Eric Dier gave away a penalty 10 minutes into the game after clumsily swinging his foot to stop Fabinho from getting a shot away, but his goalkeeper Hugo Lloris was the saviour as he stopped Radamel Falcao's penalty from sneaking into the bottom corner.
Despite failing to convert from the spot, Monaco continued to produce waves of attack as Benjamin Mendy, who had plenty of joy down the left, cut inside before taking a shot, but Lloris denied him a goal.
A few minutes later, Mendy was involved again as he found Valere Germain with a cross towards the back post, but the forward's free header hit Kevin Wimmer in the chest.
Kane's first real opportunity of the match came when Dele Alli's one-touch pass found him in the box, and with a swift turn, he unleashed a shot towards the bottom right corner, but it drifted wide.
In a very open first half, Germain showed quick feet as he got in behind the Spurs defence to pick up the long ball, and as he aimed towards the far corner from a tight angle, the ball just trickled past the outside of the post.
After the break, Monaco got the goal that they had been hunting for when Mendy cut inside from the left, dropped his shoulder and crossed to Sidibe, who fired a powerful header past Lloris from the centre of the penalty area.
Just three minutes later, Tottenham got themselves back into the game when Alli won a penalty after being caught by Kamil Gilk while trying to bring the ball down from the air.
Kane stepped up to take it, and despite the keeper getting both hands on the ball, the striker found the back of the net to score his fourth goal in five matches.
The joy lasted just 38 seconds, though, as Monaco regained their lead from the restart thanks to Lemar, who was unmarked when he struck from a tight angle to send the ball into the bottom right corner.
Lloris pulled off a handful of important saves in a bid to keep Spurs in the game, with one of them preventing Gilk's volley from smashing into the net from five yards out.
It looked like a certain goal, but Lloris showed quick reflexes to send the ball over the bar, and a few minutes later he denied Falcao's shot after the Colombian was played through on goal by Bernardo Silva.
Tottenham had glimpses at goal as the minutes ticked by, with substitutes Vincent Janssen and Christian Eriksen combining. The former held the ball up before finding the Dane on the left-hand side.
Eriksen switched feet before firing towards goal, but it was deflected behind for a corner, which resulted in Dier's header being cleared off the line by Lemar.
Alli squandered a chance with four minutes of normal time on the clock after his attempt at the far post glanced inches wide of the post.
In the end, Monaco were able to see out their win relatively comfortably to secure their place in the knockout rounds, alongside Bayer Leverkusen.
