Goals in each half from Jimmy Floyd Hasselbaink and Stuart Parnaby gave Middlesbrough FC the upper hand in their UEFA Cup Round of 32 tie although Danijel Ljuboja's powerful late free-kick kept VfB Stuttgart in contention.
The visitors weathered an early storm at the Gottlieb-Daimler-Stadion before taking the lead against the run of play in the 20th minute, as Hasselbaink raced through to drive the English side in front. Stuttgart fell further behind seconds after half-time as Parnaby turned in George Boateng's cross to put the English team in command, before Ljuboja revived home hopes with four minutes remaining.
New Stuttgart coach Armin Veh had said that his players were short of confidence, but the way his charges began the match belied their run of four matches without a win. As early as the second minute Boateng conceded possession to Ljuboja, who forced Mark Schwarzer to palm away his shot. Stuttgart continued to offer the greater threat in the opening exchanges, with Jesper Grønkjær posing a constant problem down the right while Jon Dahl Tomasson turned a shot just past the post from Ljuboja's low centre.
Ljuboja then narrowly failed to connect with Grønkjær's right-wing cross and seconds later the visitors took the lead. Fernando Meira's attempted clearance cannoned off Boateng's back and fell perfectly for Hasselbaink, who advanced to drill a left-foot shot through Timo Hildebrand's legs and into the net. As Veh had feared, the goal visibly deflated the home side, although Zvonimir Soldo did flash a volley just past Schwarzer's right-hand post.
Stuggart's plight worsened less than a minute into the second period as Boateng broke free down the right and pulled a low cross back to Parnaby who turned it past Hildebrand. Stuttgart gradually regrouped, however, and Ljuboja forced Schwarzer into action with a header before finally beating the Middlesbrough goakeeper in the 88th minute, curling his free-kick into the corner of the net - the first goal Boro have conceded in this season's competition. Both teams will have one player suspended for Thursday's return at the Riverside stadium, Emmanuel Pogatetz and Meira each collecting yellow cards tonight.