Their white shirts, soaked by the evening’s relentless rain, hung heavy and loose as they celebrated in front of Elland Road’s Don Revie stand.
The torrential downpour had aided Leeds United’s winning goal, with Lee Bowyer’s 88th-minute shot from 30 yards slipping out of Dida’s grasp, between the AC Milan goalkeeper’s legs and across the goal line as he stumbled into the post.
It was a fortunate climax to a dark and dreary Champions League night in September 2000, but it was a hard-earned and well-deserved victory for David O’Leary’s vibrant young side.
“The city was rocking,” O’Leary tells BBC Sport. “The city built up to look forward to the game. They just couldn’t wait for it.
They joined in with us, gave us brilliant support. All-day you could feel everybody couldn’t wait to get to the stadium that night. It was an amazing atmosphere.”
“It was a great night. Elland Road was packed, dancing,” full-back Ian Harte says of the famous win against a Milan side containing Andriy Shevchenko, Paolo Maldini, and Oliver Bierhoff.
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“It had rained all day. It was very, very wet. They had unbelievable players in their team, but it was that little bit of luck that you need.”
The 35,000 Leeds fans exultant beneath the floodlit shower that night could have been forgiven for allowing themselves to believe the good times had arrived and were here to stay.
Little did they know, financial mismanagement would see most of these players – a blend of gifted, energetic youngsters and ready-made, expensively acquired stars – sold off and the club relegated three seasons later.
Ultimately, their Champions League run in 2000-01 was the apex of the Yorkshire club’s era of speculative spending. And, the first of a series of highs, the Milan win breathed momentum into a campaign in which they repeatedly defied the odds to outlast many of the continent’s most powerful and iconic clubs.
These unlikely triumphs live long in the memory of many Leeds fans, but they are so distant now, separated from the present by such a long period of struggle in the second and third domestic tiers, that an entire generation of supporters can scarcely comprehend their club as a European force of the recent past.
After overcoming 1860 Munch in a qualifier – a 3-1 aggregate triumph complicated by seven first-team injuries and first-leg red cards for Eirik Bakke and Olivier Dacourt – the group-stage draw pitted Leeds, back in the Champions League for the first time since 1992-93, against Barcelona, Milan, and Besiktas.
“If somebody had said to me in August in Munich, after we won to go through, that we’d be in the semi-final in May time, no, I’d have found that very, very hard to believe,” O’Leary says, remembering the mammoth task his team faced.
The first round of fixtures delivered a humbling 4-0 defeat at the Nou Camp by a Barcelona side who, although far from a vintage crop, counted the talents of Patrick Kluivert, Marc Overmars, and former World Player of the Year Rivaldo among their number.
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“I think that was a wake-up call,” Bakke says. “That match was good for everybody to see that European football was different from English in the style of play.”
“It was probably a blessing that that happened to us,” suggests Harte, who took advantage of the Nou Camp’s tunnel-side chapel to appeal to the heavens before kick-off.
“It kicked us on. Of course, you’re gutted that you’re losing – not losing, being battered – by a top side like Barcelona. But it just goes to show the character within the dressing room that we were capable of beating Besiktas and AC Milan.”
After Milan was vanquished in the rain, Besiktas were hammered 6-0 at Elland Road. Following up on his late winner against the Italians, Bowyer was again the standout performer, scoring the first and last goals of the rout.
In the midst of the most productive season of his career, Bowyer, along with team-mate Jonathan Woodgate, was on trial after being charged with causing grievous bodily harm with intent and affray following a nightclub altercation in January.
The public and protracted case hung as heavily over the campaign as the grey Yorkshire skies on the night of the Milan win. The second trial in 2001 returned a not-guilty verdict for Bowyer and convicted Woodgate of affray.
Although he feels his team never allowed it to negatively impact their Champions League efforts, O’Leary acknowledges that the rumbling court drama was an unwelcome sideshow.
“There was so much going on behind the scenes. It was always there,” he explains. “You had to keep dealing with it all the time. It was something that you definitely didn’t need because it was such a diabolical distraction.
“It was a very difficult time. The way the players were performing under such a distraction was a great credit to them.”
“Lee was flying in on helicopters for every match, and then scoring goals,” Bakke recalls. “He was very strong mentally and very sure that he hadn’t done anything. I think the boys handled it well and the club handled it well.”
In the penultimate group fixture, after securing a 0-0 draw away to Besiktas, Leeds almost exacted revenge in their return date with Barcelona, only for a Rivaldo strike in the dying seconds to salvage a draw for the visitors.
But the result was enough to ensure a point in their final game, against Milan in the San Siro, would see Leeds through to the competition’s second group stage.
The trip to Milan came just four days after Leeds’ classic 4-3 victory over Liverpool in the Premier League, a result which, Bakke admits, was celebrated with “a good night out”.
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The focus was quickly regained for the chance to secure second-round qualification on one of European football’s grandest stages.
“I remember watching Paul Gascoigne when he played in Italy. You get to AC Milan, the San Siro, and it’s unbelievable to be playing on that pitch,” Harte says.
Shevchenko hit the post with a first-half penalty as Leeds rode their luck to score first, through a Dominic Matteo header, just before the break.
Serginho equalized for Milan in the second half, but O’Leary’s side clung to the point they’d targeted. With progress attained, the throng of traveling Leeds supporters stayed long after the final whistle to celebrate in the stands of the famous arena.
“Everyone talks about that night in Milan, singing songs with the fans,” Bakke says. “If you ask most of the players, that was the highlight of the Champions League.”
“There was a great bond between the traveling supporters and the team,” adds O’Leary “We really appreciated what they were doing. They were memorable nights.”
The draw for the second group phase was no kinder to Leeds than the first, pitting them against the other La Liga giant, Real Madrid, Italian champions Lazio – managed by Sven-Goran Eriksson and boasting such world-class stars as Pavel Nedved, Juan Sebastian Veron and Hernan Crespo – and Anderlecht. Having navigated an equally fearsome group once already, though, Leeds were unperturbed.
“We realized we could compete after we got out of the first group stage and we thought we could go on,” Woodgate says. “Thinking about it now, Barcelona, AC Milan, and Besiktas was probably harder than the second group stage.”
“That group of players, with the support of the fans and the city behind us, no matter who we played at Elland Road, we felt like we were going to go out there and win,” Harte adds. “At the start, they probably didn’t know much about us. But by the end they definitely did.”
Much like the first group, Leeds had to rebound from disappointment in the opening game; this time, while depleted by injuries, they were beaten 2-0 at Elland Road by reigning European champions Madrid.
They bounced back in emphatic style, though, winning their next three group games, significantly beating Anderlecht twice in back-to-back matches after a 1-0 win over Lazio in Rome.
O’Leary’s young side then boosted their burgeoning reputation at the Bernabeu, albeit in a narrow 3-2 defeat, before playing out a pulsating 3-3 draw with Lazio, safe in the knowledge their place in the last eight had already been clinched.
“As individuals, the other teams maybe had better players,” Bakke says. “But as a team, the hunger and fighting for each other, the spirit we had was second to none. It was in the Leeds culture. The heart has to be outside the shirt.”
“There was a great buzz around the city,” O’Leary adds. “You couldn’t wait for the next match to come along. Everybody was amazed at how far we were going.”
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Not dissimilar to Leeds’ plight in the time since Deportivo La Coruna have fallen a long way from their revered standing within Spanish and European football around the turn of the millennium.
After they’d been drawn against Leeds in the quarter-final, the Premier League side’s scouting reports would have spoken warily of the La Liga champions and the talents of playmaker Juan Carlos Valeron, Brazilian enigma Djalminha and Dutch goal machine Roy Makaay.
Before the first leg at Elland Road, Makaay had called Leeds the “weakest link” remaining in the competition. But, riding a nine-game unbeaten streak in the Premier League, the West Yorkshire side was typically ebullient in the face of fearsome opposition.
With goals from Harte, Alan Smith, and Rio Ferdinand, they produced one of the finest European performances in the club’s history. “Three-nil to the weakest link,” sang the Elland Road faithful.
“That was probably the best game I’ve ever been involved in,” Harte recalls, “winning 3-0 at home, knowing that we’d played against a really, really good side.”
Their work wasn’t done, though. Deportivo rallied and led 2-0 at the Riazor with 17 minutes still to play. “It was all about hanging in there,” Bakke remembers. “They were bombing on from all sides. Nigel Martyn was stopping everything.”
Leeds prevailed through the onslaught and booked a semi-final berth. Valencia, the previous season’s beaten finalists who had eliminated Arsenal in the last eight, lay in wait.
“We were always the underdogs so no-one expected us to get that far,” Woodgate says. “Getting to that stage, you think, ‘Can we make history?'”
A goalless first leg at Elland Road left hope alive before the two sides reconvened at the Mestalla six days later. In the interim, however, Bowyer was suspended upon review of an alleged stamp on Valencia’s Juan Sanchez.
And Leeds, perhaps showing the first signs of fatigue in the final stages of a long and exhilarating season, saw their 13-game Premier League unbeaten streak ended by Arsenal.
When Sanchez scored Valencia’s first with his arm, the wind left Leeds’ sails; they had no answer as Sanchez added a second and Gaizka Mendieta fired in a third. Out of thrust. Out at last.
“Everybody in the stadium could see that he scored with his hand,” says Harte. “We were all devastated and gutted, but we’d had a taste of the Champions League and every player involved in that run absolutely loved it.”
The heartache of Leeds’ Champions League exit was compounded by the fact they missed out on qualification for the following season’s competition by a single point, finishing fourth in the Premier League when only the top three clubs earned a seat at Europe’s top table.
And that failure to clinch Champions League football for the 2001-02 season would have long-lasting consequences. Without the financial benefits of Champions League participation, Leeds’ big-spending gamble on success came up short, putting the wheels in motion for the downturn the club is only now beginning to recover from.
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“The big players, like Rio and everyone, wanted to go and play in the Champions League, and it went down from that,” Bakke laments. “The small differences in football – if we’d have got into the Champions League, maybe we would have survived longer.”
“As a footballer,” Harte concludes, “when you hang up your boots, you want to look back and say, ‘I won that, I won this, or I achieved this’. The sad thing is, with the group of players we had, we never achieved anything.”