Boudewijn Zenden opened the scoring for the visitors early in the second half, only for Mario Bazina to level three minutes past the hour. Parity lasted only a matter of moments, however, Jimmy Floyd Hasselbaink quickly restoring the visitors' lead only for Austrian international Roland Kollman to score a second equaliser. That potentially crucial goal was undermined, however, by Kollman's subsequent dismissal for a second bookable offence and having scored two away goals the English Premiership side will be confident of progressing.
 The opening period had proved far less open. With GAK taking time to readjust to playing competitive football after a two-month winter break and Middlesbrough having to adapt to the sub-zero conditions, it was little surprise that the game took a while to warm up. James Morrison was a lively presence for the visitors down the right in the early stages, but, long-range efforts from Michael Reiziger and Ray Parlour aside, Middlesbrough rarely troubled the home goal. GAK had the better of the chances but only when their opponents' concentration slipped.
 Central defender Anton Ehman went close with a near-post header from Kollman's free-kick on 21 minutes but the best chance of the half fell to Imants Bleidelis after Franck Queudrue and Gareth Southgate had challenged for the same ball. However, with only Mark Schwarzer to beat, the Latvian debutant dragged his shot wide.
 McClaren brought about a change in attitude from his players after the break. They began playing with more ambition and were quickly rewarded. On 51 minutes Zenden picked up Queudrue’s pass on the left and sprinted forward, cutting inside before shooting inside the near post from the edge of the box.
 The goal momentarily deflated the hosts but they were soon pushing for an equaliser. Chris Riggott’s misplaced pass allowed Kollman to pick out Bazina in the box, but the Croatian was denied by a fine Schwarzer save. The Australian goalkeeper was less tidy as Middlesbrough conceded an equaliser on 63 minutes though, allowing Bazina to beat him at his near post.
 GAK enjoyed parity for all of two minutes. With the crowd still celebrating, Hasselbaink found Downing on the left and the England international beat his man before crossing for the Dutch striker to head in from close range.
 The home team were not lying down, though. With 12 minutes to go, Parlour conceded a free-kick on the edge of the area and Kollman stepped up to bend a left-footed shot beyond Schwarzer. However, his pleasure at scoring was short-lived: two minutes later he was shown his second yellow card of the night, this time for simulation. The dismissal now means he will be suspended for the return leg, at the Riverside stadium next Thursday.