On This Day: Leeds United 1-0 AC Milan

September 19, 2000: Twenty-five years ago tonight, Elland Road witnessed one of Leeds United’s most famous European nights, as David O’Leary’s side stunned Italian giants AC Milan with a dramatic late winner in the UEFA Champions League.

In a rain-soaked battle under the Elland Road floodlights, it was Lee Bowyer who struck the decisive blow, though in truth it owed everything to a costly mistake from Brazilian goalkeeper Dida. With just two minutes left on the clock, Bowyer’s speculative 30-yard effort should have been a routine save, but Dida fumbled the wet ball and stumbled backwards as it rolled over the line. The stadium erupted, and Leeds United’s Champions League hopes were suddenly alive again.

Leeds United Bounce Back After Barcelona Defeat

The victory came at a crucial time for Leeds. Only a week earlier, O’Leary’s young side had been thrashed 4-0 by Barcelona at the Nou Camp, raising doubts about their ability to compete in Europe’s elite competition. To make matters worse, the Whites were dealing with a lengthy injury list and had to cope without star striker Mark Viduka, away on Olympic duty with Australia.

But against a Milan side boasting legends such as Paolo Maldini, Oliver Bierhoff, and Andriy Shevchenko, Leeds produced a display full of resilience, energy, and spirit.

Matteo’s Debut and a Midfield Battle

One of the night’s big surprises was the inclusion of Dominic Matteo, who made his debut after a £4.25m move from Liverpool. Despite only just recovering from a knee injury, Matteo slotted in superbly and was one of Leeds’ standout performers. Alongside Olivier Dacourt and Bowyer, the midfield refused to give Milan any comfort.

Eirik Bakke twice went close in the first half, missing a golden header from eight yards, while Leeds defended with discipline to keep Bierhoff and Shevchenko largely at bay.

Shevchenko’s Miss and Bowyer’s Moment

Milan’s best chance came in the 76th minute when Shevchenko pounced on a defensive error, only to pass to Bierhoff, who was clearly offside. It was a let-off that proved decisive.

Then came the moment Leeds fans will never forget. Bowyer, ever the driving force in midfield, unleashed a hopeful strike that skidded off the sodden turf. Dida spilled it, then clumsily carried it into his own net. The Elland Road faithful exploded with joy, their earlier frustration from a league defeat against Ipswich Town washed away in the rain.

25 years ago tonight, Lee Bowyer with the winner on an incredible night against AC Milan 🤩 #LUFCpic.twitter.com/sjNCNtctQv

— LUFCMOT (@LUFCMOTcom) September 19, 2025

European Dreams Restored

The 1-0 win not only restored pride after the Barcelona humiliation but also reignited Leeds United’s Champions League campaign. With Barcelona losing to Besiktas on the same night, the group suddenly opened up again.

For O’Leary, whose patched-up side had been written off before kick-off, it was a result that showed the resilience and belief of his young squad. The victory over AC Milan remains one of the defining moments of Leeds’ famous 2000/01 Champions League run, a campaign that would eventually carry them all the way to the semi-finals.

Leeds United Line-Up vs AC Milan (2000)

• Leeds United XI: Martyn, Kelly, Harte, Duberry, Mills, Bowyer, Bakke, Dacourt, Matteo, Bridges, Smith.
• AC Milan XI: Dida, Chamot, Costacurta, Maldini, Helveg, Albertini, Giunti, Coco, Guglielminpietro, Bierhoff, Shevchenko.