Late goals from substitute Yevgen Seleznov and Jadson gave FC Shakhtar Donetsk a useful first-leg advantage over Tottenham Hotspur FC in freezing conditions at the RSC Olympiyskiy Stadium.
Seleznov, who replaced Olexandr Gladkiy up front for Mircea Lucescu's charges, brought the game to life when he rose highest to flick Jadson's free-kick past Heurelho Gomes with his first touch on 79 minutes. Jadson then extended the lead with two minutes to play via a clinical finish after a clever exchange of passes with Willian.
Only Jermaine Jenas and Michael Dawson retained their places from the team which drew 0-0 against Arsenal FC in Tottenham's last match and Shakhtar almost profited from the unfamiliarity in Harry Redknapp's ranks early on. A fortuitous deflection handed the game's first chance to Jadson but his volley on the turn drifted comfortably wide while Răzvan Raţ skied over from a narrow angle.
Spurs were thankful when Gladkiy fired a presentable chance wide midway through the half but they slowly gained a foothold in the contest and nearly opened the scoring when Giovani Dos Santos bent their first effort into the sidenetting on 32 minutes. Jadson called Gomes into action from distance just before the break but it was an otherwise quiet half for the Brazilian custodian.
Confusion in the Spurs penalty box provided Willian with a sight of goal but he pulled his effort wide of the far upright while Jenas could not retain his balance after clipping the ball past goalkeeper Andriy Pyatov at the other end at the start of the second half. Tottenham's 17-year-old debutant Dean Parrett forced Pyatov to save at his feet before the two late strikes changed the course of the tie ahead of the second leg at White Hart Lane next Thursday.