After a goalless game at the Stadio Olimpico a week previous, the tie was in the balance when AS Roma arrived at Elland Road on March 9, 2000.
With the Premier League title challenge slipping away and early exits from the FA Cup and the League Cup, it meant the competition was United’s only real hope of silverware.
Fans were left dreaming as Italian giants Roma were added to the sides Leeds had brushed aside in the competition with Partizan Belgrade, Lokomotiv Moscow and Spartak Moscow defeated in the earlier rounds.
After a cagey first leg, which saw superb defensive displays from both sides, the second leg started in similar style with limited goalscoring opportunities.
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Roma striker Francesco Totti was the Italian’s most likely source of creativity with his passing and movement being at the heart of almost every Roma move.
Michael Bridges and Harry Kewell struggled to break down the Roma defence as Stephen McPhail and Jason Wilcox’s overlapping runs created Leeds’ best chances.
Kewell saw a shot pushed wide while Eric Bakke had an effort saved.
Midfielder Lee Bowyer squandered a promising counter-attack as his weak effort rolled wide.
Although Nigel Martyn had very little to do, Roma wasted numerous openings with Allesandro Rinaldo and Vincenzo Montella both unable to hit the target before veteran defender Aldair saw his headed chance go over the bar.
Leeds would have fallen behind if not for strong performances from the back three of Lucas Radebe, Gary Kelly and Alfie Haaland.
At half-time, 135 minutes still couldn’t seperate the sides with extra-time and penalties a distinct possibility.
But the deadlock was finally broken in the 67th minute as Haaland played in Kewell who rifled home past a despairing Francesco Antonioli to send the home fans into raptures.
With Roma pushing for an all important equaliser which would have seen them through on the away goal rule, the game became bad-tempered.
Haaland was lucky to remain on the pitch for his late tackle on Marco Delvecchio.
The game then turned ugly as it entered stoppage time.
Substitute Alan Smith and Zago were both shown yellow cards for an off-the-ball incident after a poor challenge from the Brazilian.
It was Zago’s second booking and he was ushered off the pitch following protests from Roma players.
Roma were reduced to nine players minutes later as left-back Candela appeared to head-butt Darren Huckerby leaving Garcia-Aranda Encinar with no other decision than to produce a red card.
The victory took Leeds into the last eight where they defeated Slavia Prague but their dream came to an end in the last four against Galatasary.
While they didn’t win the competition it certainly got fans dreaming of European domination as they went on to make the semi-finals of the Champions League the following season in a campaign which saw them defeat AC Milan and knock Barcelona out in the first group stage.
Leeds United 1
AS Roma 0 (United win 1-0 on aggregate)
Thursday March 9, 2000 UEFA CUP fourth round, second leg
Leeds: Martyn, Kelly, Radebe, Haaland, Harte, Bakke (Jones), Bowyer, McPhail (Huckerby), Wilcox, Kewell, Bridges (Smith).
Roma: Antonioli, Aldair, Zago, Mangone, Rinaldi, Candela, Nakata (Di Francesco), Tommasi, Delvecchio, Montella, Totti.
Referee: Garcia-Aranda Encinar (Spain).