VfB Stuttgart 1 Middlesbrough 2: Hasselbaink and Parnaby delight Middlesbrough and warn Europe

McClaren said: "You have to be organised and disciplined and we were." But the manager admitted the home side's late goal had been a blow. "A clean sheet is most important. It does leave the tie still open."

He had decided to rely on Boro's counter-attacking ability in this first leg and gambled by leaving leading scorer Aiyegbeni Yakubu, on the bench. With Mark Viduka ill and Massimo Maccarone having broken his nose in training, McClaren played with a single striker in Hasselbaink.

There was a first start in 12 games for the midfielder George Boateng and a place for the defender Andrew Davies in the absence of the injured Gaizka Mendieta and James Morrison .

The new Stuttgart coach, Armin Veh, included the former Aston Villa midfielder Thomas Hitzlsperger and Jesper Gronkjaer, once of Chelsea and Birmingham. They join-ed Newcastle old boy Jon Dahl Tomasson in the team.

Stuttgart's early build-up play was often neat and Tomasson might have scored at the near post after 16 minutes when Fernando Meira played Danijel Ljuboja in behind Emanuel Pogatetz once again, but his snap-shot flew just wide.

Ljuboja should have put the home side in front two minutes later, only to deflect Gronkjaer's cross across goal. Gronkjaer was full of invention and running down the right, but it was Boro who took the lead seconds later when Meira's clearance hit Boateng and Hasselbaink hammered the ball past the Stuttgart goalkeeper Timo Hildebrand.

That setback unnerved Stuttgart and quickly after the interval Middlesbrough added to their lead.

Boateng ghosted past an ineffectual challenge from Delpierre down the right and pulled the ball back from the byline for Parnaby, revelling in his right-sided attacking role, finished emphatically with a right-foot shot.

With Boro apparently cruising, Stuttgart cut the deficit with five minutes left from a brilliant 25-yard free-kick from Ljuboja, but the visitors held on, resisting a late Stuttgart surge.

Hasselbaink thought Boro now have a great chance to reach the last 16, saying: "We were a bit unfortunate for the last goal, but it was a very good performance and we would have taken 2-1 before the game."

VfB Stuttgart (4-4-2): Hildebrand; Stranzl (Beck, h-t), Meira, Delpierre, Gerber; Gronkjaer, Meissner (Gentner, 72), Soldo, Hitzlsperger (Gomez, 62); Tomasson, Ljuboja. Substitutes not used: Heinen, Babbel, Tiffert, Magnin.

Middlesbrough (4-5-1): Schwarzer; Davies, Riggott, Southgate, Pogatetz; Parnaby Doriva, Boateng (Kennedy, 78), Rochemback, Downing (Johnson, 70); Hasselbaink (Yakubu, 85). Substitutes not used: Jones, Bates, Taylor, McMahon.

Referee: A Hamer (Luxembourg).