Jadson caps off a fine display scoring Shakhtar's second goal
An unfamiliar looking Tottenham side conceded two goals in the last 11 minutes to leave their Uefa Cup hopes hanging in the balance.
Late goals by Yevgen Seleznov and Rodrigues Jadson put Shakhtar Donetsk in the driving seat for the second-leg.
Spurs spent most of the match thwarting their lively hosts but with 10 minutes left Jadson floated in a free-kick for Seleznov to nod in powerfully.
And Jadson made it 2-0 after a mazy run to poke home past Heurelho Gomes.
Defenders Michael Dawson and Pascal Chimbonda impressed, while Giovanni had Spurs' best chance in the first half.
It was Tottenham's first of six games in 17 days, including a Carling Cup final at Wembley - a schedule boss Harry Redknapp describes as "crazy", and there was a cautious feel to the Spurs team selection.
Only Jermaine Jenas and Dawson remained from the team that drew with Arsenal last weekend with Darren Bent having to watch from the bench, with Fraizer Campbell playing as the lone striker.
Shakhtar manager Mircea Lucescu predicted the match would be "good Brazilian flair against English physical strength" and the opening 20 minutes proved his statement to be only half correct.
The hosts, on a winter break and without a game since a 3-2 win at Barcelona in the Champions League on 9 December, had four Brazilians in their team and their possession and creativity meant their opponents spent the majority of the first-half chasing shadows.
After just three minutes Jadson pushed a shot wide and the industrious Fernandinho then floated in a delightfully-weighted cross for Razvan Rat who blazed over.
It should have been a wake-up call for the Tottenham defence but they continued to doze and with Shakhtar's movement incessant, Olexandr Gladkyy and Mariusz Lewandowski both wasted good chances from six yards.
It took a full half an hour before Tottenham's first meaningful break when Giovanni burst down the left to unleash a shot against the side netting.
It seemed to encourage Spurs to venture further forward and with Jenas increasingly influential, David Bentley wasted a free-kick from 25-yards.
Shakhtar were the first side to threaten in the second half and Willian had a great chance when free on the left but dragged his shot wide.
As the game progressed and the home crowd more and more impatient, Tottenham grew in confidence and begun to pass the ball around with ease, instead of the long-ball policy they used in the opening period.
Fernandinho sent a free-kick flying high into the crowd, but Spurs looked the more likely to score and 17-year-old Dean Parrett almost marked his debut with a goal, only to be denied by the legs of keeper Andriy Pyatov.
Just as Spurs looked as if they might escape with a goalless draw, Didier Zakora conceded a free-kick on the edge of the box.
Up-stepped Jadson who crossed over a static defence to find an unmarked Seleznov to nod in past a flailing Gomes to score with his first touch of the game after coming on as substitute.
An inability to deal with crosses has been a weakness of Gomes' this season and his failure to punch the ball before Seleznov will not have helped his cause. It was an incident that saw the keeper needing extensive treatment for a knock.
Tottenham's heads dropped and Brazilian Jadson picked up the ball down the right and after dancing around four defenders, played a one-two, before slotting in from 10 yards to secure the win.
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