Stuttgart 1 Middlesbrough 2: Middlesbrough produced a classic away performance in Germany to take a massive stride towards the last 16 of the UEFA Cup for the second successive season before being pegged back late in the game.

Jimmy Floyd Hasselbaink fired the visitors ahead at the Gottlieb-Daimler Stadium against the run of play with 20 minutes gone, but after Stuart Parnaby doubled the lead with his first European goal, the Germans wilted alarmingly before Danijel Ljuboja’s 85th-minute free-kick reignited the tie just when it looked as though the Teessiders had killed them off.

Stuttgart will arrive at the Riverside Stadium next Thursday evening knowing a seventh clean sheet for Boro in eight European games - they had not conceded a goal in 625 minutes so far this season before the Serbian Ljuboja struck - will hand Steve McClaren’s men a showdown with either Roma or Club Brugge.

Boro look well capable of doing that after following up their heroics against Chelsea with a performance which was based on grit and not a little good fortune before the break, but knowhow and common sense after it with Hasselbaink and George Boateng, who had a hand in both goals, particularly impressive.

McClaren was even able to leave leading scorer Aiyegbeni Yakubu on the bench for all but the last eight minutes with one eye on Sunday’s FA Cup fifth-round trip to Preston, and not even a false alarm over a suspect package before kick-off could spoil the night for the 1,500 travelling supporters.

The question beforehand was which Boro would turn up - the side which capitulated so horrendously against Aston Villa, or the one which demolished champions Chelsea last Saturday? Had Stuttgart been able to apply a finish to any of the numerous chances they created before the break the game, and perhaps the tie, might have been theirs.

Former Newcastle frontman Jon Dahl Tomasson fired wide at the near post on 16 minutes, strike partner Ljuboja flicked a teasing Jesper Gronkjaer ball across the face of goal when it looked easier to score and both full-back Heiko Gerber and Ljuboja saw shots cannon into team-mates before they could trouble Mark Schwarzer.

Indeed, the Australian, who had a spell in Germany with Kaiserslautern earlier in his career, did not have a single save of note to make in the first half. Boro were forced into playing on the break, and the one real opportunity they created led to the opening goal with 20 minutes gone.

Emanuel Pogatetz chased down his own high ball and was comfortably beaten to it by Fernando Meira, but his attempted clearance hit the unwitting Boateng and rebounded to Hasselbaink, and he dispatched it past goalkeeper Timo Hildebrand without a second thought.

Stuttgart coach Armin Veh drafted highly-rated youngster Andreas Beck into his line-up at the break in place of full-back Martin Stranzl, but Boro increased their lead with less than a minute of the half gone.

The industrious Boateng powered his way past defender Matthieu Delpierre wide on the right and surged into the penalty area, where he had the presence of mind to pick out the fast-arriving Parnaby.

The specialist full-back, playing in midfield for the night, had not scored a senior goal for the club until the FA Cup third-round replay against Nuneaton Borough last month, but he gleefully rattled home his third of the campaign to give the Teessiders a precious 2-0 lead.

It could have been even worse for the Germans with Hildebrand having to block a Hasselbaink effort with his legs after the Dutchman eased past Delpierre on 56 minutes, and the goalkeeper had to save from Stewart Downing seconds later with the home side in disarray.

Their evening was summed up on 62 minutes when Gronkjaer picked out the unmarked Tomasson at the near post, but his control let him down with the goal at his mercy and the home fans started to leave the ground.
 
Boateng and then Hasselbaink made way in the dying stages as first Jason Kennedy and then Yakubu joined the fray, but they were dealt a blow with just five minutes remaining. Ljuboja took charge at a free-kick 20 yards out and hammered an unstoppable shot past Schwarzer to give his side hope for next week.