Tottenham go out of the Champions League with a whimper after another poor showing in Europe as Monaco advanced to the last-16.
After Bayer Leverkusen were held to a draw by CSKA Moscow earlier in the night, Spurs stepped out at the Stade Louis II knowing a draw would at least keep them in the fight to reach the knockout rounds going into the final matchday.
However, the north Londoners produced arguably their worst performance of the season as second half goals from Djibril Sidibe and Thomas Lemar gave Monaco the win.
Despite a below-par showing, Spurs had their chances to win the game, Heung-Min Son going close after just six minutes when fluffing his lines in a one-on-one.
Monaco were also guilty of missed opportunities in the first half, Radamel Falcao failing to beat Hugo Lloris from the penalty spot after Eric Dier had chopped down Fabinho.
Had it not been for Lloris, Monaco would have won by more, the Frenchman denying Benjamin Mendy and Valere Germain before the break.
Lloris could do nothing about Monaco’s opener three minutes after the restart though, Mendy working his way into the penalty area before floating in a cross which Sidibe powered home with his head from six yards out.
Spurs got themselves back into the game four minutes later when Dele Alli was brought down inside the box by Kamil Glik, Harry Kane stepping up to score his first Champions League goal from the spot.
The visitors were only level for 38 seconds though, Monaco going back ahead after Lemar found plenty of time inside the box to fire an angled shot in to the far corner.
It could have been more for the Ligue 1 side as Glik was denied brilliantly by Lloris, while Falcao failed to finish when one-on-one.
The result means Tottenham’s clash with CSKA Moscow is a dead rubber affair, Monaco and Bayer Leverkusen advancing from Group E.