- Tottenham are the first Premier League club to be knocked out of the Champions League this season
- Djibril Sidibe headed Monaco ahead just after half-time but their lead lasted only four minutes
- Harry Kane converted from the spot in the 52nd minute after Dele Alli was fouled in the penalty area
- But Monaco regained the lead a minute later as Thomas Lemar drove the ball into the bottom corner
- Hugo Lloris saved first half penalty from Radamel Falcao after Eric Dier fouled Henrique Fabinho in the area
The last time Tottenham reached club football's most prestigious competition they travelled as far as the quarter-finals, recorded landmark victories over both Milan clubs and witnessed the blossoming of Gareth Bale as one of the world's great players.
This time, they have been unable to record a solitary victory in four games against Monaco and Bayer Leverkusen, the teams that will qualify from Group E, and have looked uncomfortable in the surrounds of their Wembley home.
Thomas Lemar celebrates after putting Monaco back in front against Tottenham in their Champions League group match
Djibril Sidibe celebrates scoring Monaco's opening goal just after half-time alongside team-mate Valere Germain
Monaco players celebrate re-taking the lead and tightening their grip at the top of Champions League Group E
Djibril Sidibe powers his header past the despairing dive of Hugo Lloris to give Monaco a deserved lead against Tottenham
Hugo Lloris gestures at his defence after Thomas Lemar was left unmarked in the penalty area to fire the winner for Monaco
Harry Kane shows his frustration as team-mate Dele Alli puts his head in his hand after Spurs conceded their second goal
Victor Wanyama, Eric Dier, Harry Winks and Hugo Lloris look dejected after Spurs fell behind straight after half-time
Dele Alli is fouled by Kamil Glik as he looks to turn away from the Monaco defender to earn Tottenham a second-half penalty
Harry Kane brings Tottenham level despite the best efforts of Monaco shot-stopper Danijel Subasic in goal
MATCH FACTS, RATINGS AND MATCH ZONE
This was a huge game for them, victory essential once Leverkusen had earned a point in Moscow, but it never looked likely. Monaco missed a penalty, were the better team in the first-half, took the lead, and then, when Tottenham equalised, went ahead again within 39 seconds.
It was a deserved victory, worthy of group winners and with their enterprising, lively style Monaco will be a handful for whoever they draw in the last 16.
All Tottenham have to look forward to from here is the Europa League, presuming they win that last game, and while the prize at its end is great, some consider Thursday night football a curse for those with title ambitions. Even this setback will have taken it out of them with a huge match against Chelsea scheduled for Saturday.
No decision has been made on whether Tottenham will return to Wembley in reduced circumstances in the New Year. Tottenham have already sold 80,000 tickets for their last Champions League game, but how many of those will bother on the night remains to be seen.
Those making the journey to the French Riviera were left subdued, their team humbled by opponents who were sharper, braver in thought and ambition, and more resilient at the back.
To be fair a draw wasn't really good enough for Tottenham anyway, but it would at least have left them the smallest glimmer of hope. Leverkusen and Monaco could as good have carved up the group, but at least Tottenham would still be in there fighting.
Defeat was the end, though – and a desperately disappointing one considering the optimism around their progress when the draw was made.
Yet Tottenham have been more than matched in Europe so far. Last night, an unfamiliar defensive formation rarely looked comfortable, and Monaco could have won by more. They missed a penalty, several good chances and Hugo Lloris made outstanding saves.
Yet despite this, the game, and Tottenham's fate, hinged on five minutes of madness in which Pochettino's side were out of the Champions League, back in clinging by the fingertips, and then out again – this time for good.
Between the 48th and 53rd minutes, three goals were scored and Tottenham's frailty exposed. They simply couldn't cope with Monaco's speed and energy down the flanks and, having equalised, were behind again within a minute.
Pochettino looked livid but questions will be asked about his decision to play three at the back, with Victor Wanyama a forward sweeper, resting the reliable Jan Vertonghen. At no time did Tottenham look comfortable with Monaco's forwards – despite a less than convincing display by Radamel Falcao.
If ever endorsement of Monaco's fluid style of play was needed it came with the first goal – a cross by their left full-back, converted by the right full-back, while standing in the position more commonly occupied by the centre-forward