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A superb double from Bryan Mbeumo helped Brentford come from behind to win and spoil Tottenham's final home game of a miserable season.
Mbeumo struck two fine efforts into the far corner early in the second half, before team-mate Yoane Wissa capped things off, as Brentford overturned Tottenham's first-half lead which had come via captain Harry Kane.
Just days after strike partner Ivan Toney was banned for eight months for breaking Football Association betting rules, Mbeumo showed Brentford fans they can count on him to deliver the goals.
It had been a moment of magic from Kane, whose future at Spurs remains in question, when he curled the ball beautifully into the top corner from a free-kick.
It galvanised his team-mates and they played with confidence and flair, creating numerous chances which they should have put away.
Their lack of ruthlessness was punished though as Brentford responded immediately in the second half - Mbeumo taking his chances, firing past goalkeeper Fraser Forster twice in 12 minutes.
Any chance of a late equaliser by Tottenham evaporated when substitute Shandon Baptise robbed Oliver Skipp of possession and Mbeumo teed up Wissa for a comfortable finish.
It was another performance which summed up Tottenham's season - moments of promise before a crushing result.
"The intensity dropped quite a lot in the second half," said interim boss Ryan Mason. "We needed to take our opportunities when they came in the first half.
"They really took theirs. It's difficult to take. It's not just one half of football, you have to do it for the full game."
Tottenham's extremely slim hope of European qualification is fading rapidly, while Brentford know they will finish a successful season inside the Premier League's top 10.
"In many ways it is unbelievable what we have achieved so far this season. Hopefully there is a bit more," Brentford manager Thomas Frank told BBC Sport.
"Maybe, maybe we can push it on the last day and go into Europe. But just a top 10 finish secured, maybe eighth or ninth, we don't know but that is unbelievable."
With very little to play for, most of the focus pre-match was on Kane and his Tottenham future as fans visited the newly-painted mural of their record goalscorer across the road from the stadium.
It was his 300th start in the Premier League for Tottenham but how many more will be added to that tally remains unknown.
He was a bright spark in the early stages alongside Son Heung-min, who himself had several chances to score in the first half.
Brentford's Rico Henry made a crucial goalline clearance to deny Emerson Royal and Arnaut Danjuma flicked a diving header inches wide from Son's cross.
Bar a few half-chances and a dangerous cut-back from Kevin Schade, Brentford did little to trouble goalkeeper Forster until the second half.
But they started on the front foot after the break, getting in behind Spurs' defence and feeding Mbeumo, who took both of his goals extremely well.
From then on, the atmosphere inside the stadium changed as the familiar feeling of defeat crept in and Brentford's support sang teasing chants to increase the pain.
Just as Tottenham began to test Brentford's defence again, Skipp unforgivably lost the ball on the edge of his own box and Tottenham were punished, Wissa coolly stroking it past Forster.
A late header from substitute Richarlison in stoppage time was superbly tipped over the bar by David Raya but some Tottenham fans had already started exiting the stadium - many of them not stopping for a pre-planned lap of appreciation to mark the final home game of the season.
