The Togolese striker netted twice in four second-half minutes to turn the tie on its head after Christian Eriksen's free-kick had cancelled out Roman Zozulya's openerEmmanuel Adebayor inspired Tottenham to a stirring comeback against Dnipro Dnipropetrovsk at White Hart Lane and a place in the last 16 of the Europa League.
Roman Zozulya headed in Yevhen Konoplyanka's free-kick on 47 minutes to put the Ukrainian giants two goals in front on aggregate, but Christian Eriksen's free-kick pulled the hosts level on the night.
And Adebayor struck twice in four minutes after Zozulya had seen red for headbutting Jan Vertonghen to turn the tie on its head and fire Tim Sherwood's men through.
|VIEW FROM WHITE HART LANE
|By Greg Stobart
Even if Tim Sherwood loses his job to Louis van Gaal in the summer, he will still have some special memories to remember from his time as Tottenham manager.
This will be one of them. Spurs now face Benfica in the last 16 of the Europa League - and now it no longer feels like a Mickey Mouse competition.
They were in big trouble when Roman Zozulya put Dnipro ahead on Juande Ramos’ return to White Hart Lane but the striker’s red card was undoubtedly the key moment of the game.
Jan Vertonghen made the most of the contact but it was a stupid act by the Ukrainian striker, with the score 1-1 at the time after Christian Eriksen’s superb free-kick.
The atmosphere at White Hart Lane was as loud as I’ve heard it this season during that 15-minute spell in the second half as Spurs turned the tie on its head, inspired by Eriksen and Emmanuel Adebayor.
Adebayor eventually made the difference with two expert finishes, and while Spurs top-four hopes are fading, they still have plenty to look forward to in the Europa League under Sherwood.
But despite the more adventurous selection, it was 25 minutes until the hosts managed a meaningful effort on goal - Eriksen's 30-yard free-kick comfortably saved by Denis Boyko low down to his right.
After a first half devoid of action, the hosts suffered a nightmare start to the second period, Zozulya stealing in unmarked to head home Ruslan Rotan's whipped free-kick from the left.
Rather than deflate them, the goal appeared to spark Spurs into life, Mousa Dembele thumping a shot into the turf and onto the roof of the net, before Roberto Soldado's first-time effort was denied by an offisde flag.
Eriksen did pull one back in the 56th minute, sending a dipping free-kick around the wall and into the bottom left-hand corner, despite Boyko's strong hand.
The second half was unrecognisable from the turgid fare on offer in the first, former Tottenham target Yevhen Konoplyanka curling a low effort against the post from 25 yards with Hugo Lloris beaten.
Shortly after the hour, Zozulya put his side under unnecessary pressure by headbutting Vertonghen as Dnipro prepared to defend another Eriksen set-piece.
Ten minutes later, two goals from Adebayor turned the tie completely on its head.
Eriksen was involved yet again for the first, sending in a devilish low ball for the Togolese, who sprung the offside trap and tapped home from six yards.
Four minutes later Spurs were ahead for the first time in the tie, Ezekiel Fryers sending a long ball forward which Adebayor controlled beautifully on his chest before poking the ball beyond Boyko.
Tottenham held on comfortably in the final stages to set up a last-16 tie with last year's runners-up Benfica, although they will be without their record goalscorer in European competition Jermain Defoe, who bid farewell to the home fans at half-time ahead of his move to MLS outfit Toronto.