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.
After returning to the Europe’s elite competition for the first time since the 2010/11, Tottenham now depart with their legs in between their tails following a campaign that has left plenty to be desired.
Monaco, meanwhile, are now guaranteed to go through as group winners with Leverkusen, who had earlier drawn 1-1 with CSKA.
So how did the two teams fare? See the gallery above for our player ratings.Reuse content