Kane's not able to save his Spurs
Striker slams 'schoolboy' errors in Monaco defeat
Hugo Lloris' penalty heroics could not rescue Tottenham's Champions League campaign as Mauricio Pochettino's men slipped to a 2-1 defeat against Monaco.
The result means Spurs cannot progress from Group E and need a point against CSKA Moscow at Wembley next month to finish third and qualify for the Europa League.
Lloris denied former Manchester United and Chelsea striker Radamel Falcao's spot-kick in the first half and made a number of superb saves but second-half goals from Djibril Sidibe and Thomas Lemar gave Monaco a deserved victory.
Harry Kane offered Tottenham temporary hope when he equalised from the penalty spot but the visitors simply never found the spark required to resurrect their faltering fortunes in Europe.
Monaco, meanwhile, are now guaranteed to go through as group winners with Leverkusen, who had earlier drawn 1-1 with CSKA.
Son Heung-min could have given Tottenham the perfect start when he was played through one-on-one by Alli but as he tried to go around goalkeeper Danijel Subasic, the South Korean took a heavy touch and the chance was gone.
That was as good as it got in the first half for the visitors, who should have fallen behind five minutes later when Victor Wanyama and Eric Dier both took wild swings at the advancing Fabinho, with Dier connecting to concede a penalty. Falcao has scored five goals in his last three matches but was unable to capitalise as Lloris guessed correctly by diving low to his right and palming the ball away.
Spurs were rattled. They were careless in possession and frantic at the back, as a rampant Monaco forced mistakes and broke through almost at will.
Whatever Pochettino said during the interval, there was little change after the restart as three goals flew in during a lively four minutes.
First, Sidibe headed home from close range after Mendy had left Winks for dead out wide but Tottenham were level almost immediately, as Alli was pulled back by Kamil Glik and, after a long hesitation, Dutch referee Bjorn Kuipers pointed to the spot.
Kane converted, his low shot too powerful for the outstretched hand of Subasic - but Monaco needed only four passes from kick-off to unlock their opponents and again it was both full-backs involved, this time Sidibe supplying the cross for Mendy to drive home at the back post. Pochettino swivelled on his feet in frustration.
"It is disappointing. We got ourselves back in the game at 1-1 and it was schoolboy to concede straight after that," said Spurs striker Harry Kane.
"We had to try to grind out a win because we were not great tonight - the second goal took the stuffing out of us. I just don't think on the day we were good enough. I'm gutted - we wanted to go far but it is something we will have to deal with."