Tottenham were hoping to seal a champions league spot as they faced mid table side Bournemouth in their penultimate game in the Premier League.
But the unpredictable North London side were reduced to nine men for unwanted challeneges before conceding a heart breaking goal in the injury time that may prove fatal in the ultimate showdown against Everton next week.
It was a disappointing display from Mauricio Pochettino’s side, who face Ajax in the Champions League semi-final second leg on Wednesday in Amsterdam, having lost the first leg 1-0.
In-form striker Son Heung-Min got the marching order for pushing Jefferson Lerma at the end of a frantic first half, in which Eric Dier was lucky not to have been sent off and Bournemouth could conceivably have had two penalties.
Adding to the mysery of the visitors, Juan Foyth was also shown a straight red card in the 48th minute for a veil challenge on Jack Simpson just after two minutes coming on from the bench.
The Cherries struggled to capitalise their numerical advantage until Nathan Ake popped up to score a 91st-minute winner, superbly heading in from a frantic corner situation.
Bournemouth inflicted third defeat of Spurs in their last four league games to leave them on fourth in the table with 70 points .
The result gives Spur’s London rivals Chelsea and Arsenal hope in the race for the prestigious Champions League qualification. Chelsea can go third if they beat Watford on Sunday while Arsenal have to win both their remaining games and depend upon Spurs vs Everton match to seal a top four spot.