Sporting Clube de Portugal survived some nervous moments in the Estádio José Alvalade and then scored in the final minute through Pedro Barbosa to secure their passage into the UEFA Cup quarter-finals.
 Middlesbrough FC strove valiantly to get back on terms after losing the home leg 3-2 but the task proved beyond them. The visitors had to look for goals while also being aware that to concede in Lisbon would almost certainly signal their exit. It did not help that Jimmy Floyd Hasselbaink picked up an injury in training to join fellow forward Mark Viduka on the sidelines.
 With a host of other absentees severely restricting his options, manager Steve McClaren opted to pair Joseph-Désiré Job in attack with Szilárd Nemeth. The duo were lively all night but will look back on a couple of missed opportunities that could have made all the difference.
 Seizing the initiative and encouraged by Sporting's decision to leave pacy Cameroonian forward Roudolphe Douala on the bench, Middlesbrough carved out a great chance in the 16th minute. Goalkeeper Mark Schwarzer launched a massive clearance and Job did well to bring it under control, just getting the touch to nick the ball away from Ricardo. Support was offered by Nemeth and although the Slovakian kept his shot on target, Rui Jorge was able to clear off the line.
 The home team had a good spell before half-time, coinciding with Douala's introduction for the limping Hugo. After a dangerous break Chris Riggott did well to block Liedson's attempt. The move continued and Hugo Viana powered in a shot which was parried.
 A goal before the break would have boosted the visitors' hopes and they almost grabbed it as Ricardo showed both sides of his game. The goalkeeper first failed to deal with Stewart Downing's cross but when the ball spilled out to Stuart Parnaby, Ricardo then produced a strong hand to keep out the youngster's firm drive.
 The game's clearest opportunity arrived five minutes after half-time when another Ricardo mistake left his team badly exposed. His attempted clearance went only as far as Nemeth but as he squared the ball into Job's path he applied too much weight to the pass and the Cameroonian could only jab it wide.
 Knowing that Middlesbrough needed to score twice, Sporting were content to continue with their cautious approach. Their supporters were not happy with their inability to follow up their first-leg goal-spree although they did create chances in the second half with Liedson lofting over the bar.
 Middlesbrough kept pressing and threw on 19-year-old striker Danny Graham in a bid to continue their first-ever European adventure. It was Sporting however, who had the most penetration late on with Schwarzer forced into a desperate save after Gareth Southgate had deflected a cross towards his goal.