The magic of the UEFA Champions League captures the hearts of football fans the world over. With dominant performances from some of Europe’s elites to Champions League upsets, the trophy is often revered as football’s greatest club prize.
Champions League Upsets That Shook Football
Liverpool’s “Miracle of Istanbul”, Chelsea’s smash-and-grab in Munich and Marseille’s win over peak Sacchi-era Milan stand out among the greatest Champions League final shocks, with Red Star Belgrade and Borussia Dortmund also lifting the trophy against heavily favoured giants. Below is a breakdown of the five biggest underdogs to win the European Cup/Champions League, including venue, pre‑match odds, summaries and key moments.
Liverpool vs AC Milan, 2005
Atatürk Olympic Stadium
Istanbul, Turkiye
25 May 2005
Pre‑match odds
AC Milan were favourites at around 6/5 (2.20), with Liverpool out at roughly 11/4 (3.75) to win in normal time, underlining how strongly the Italian giants were expected to prevail.
Match summary
Milan’s star-studded side raced into a 3–0 half-time lead, creating far more and better chances and appearing to justify the market’s view that they would win this final almost every time it was played. Liverpool then produced one of sport’s most famous comebacks, scoring three times in six second-half minutes to force extra time before winning the trophy on penalties.
Key moments
- Paolo Maldini scored inside the first minute and Hernán Crespo’s brace put Milan 3–0 up, with the Italian side generating far higher expected goals and triple Liverpool’s shots inside the box.
- Steven Gerrard, Vladimír Šmicer and Xabi Alonso scored between the 54th and 60th minutes, turning Liverpool’s in‑play win probability from almost negligible (well under 1%) to above a third.
- In the shootout, Jerzy Dudek’s saves, including from Andriy Shevchenko, sealed a victory that most models suggest Milan would have earned in the vast majority of simulations.
Chelsea vs Bayern Munich, 2012
Allianz Arena
Munich (Germany)
19 May 2012
Pre‑match odds
Bayern, playing at home, were clear favourites at around 1.80 to win in 90 minutes, while Chelsea were out at roughly 4.33, with the draw at 3.75. Online casinos like cryptocazinos.com are always extremely busy anytime a big English club are involved.
Brief match summary
Bayern dominated territorially and on chances, repeatedly testing goalkeeper Petr Čech and missing several good opportunities while Chelsea defended deep and looked to survive. Thomas Müller’s late header seemed to settle it, but Chelsea snatched an equaliser and then rode out extra time before triumphing in a penalty shootout.
Key moments
- Arjen Robben and Mario Gómez both spurned big chances as Bayern racked up attempts, including Robben being denied by Čech and the woodwork.
- Müller finally broke through with an 83rd‑minute header, only for Didier Drogba to level from Chelsea’s first corner in the 88th minute.
- In extra time, Čech saved Robben’s penalty, and in the shootout Drogba converted the decisive kick to complete one of the most unlikely “away” wins in a final held at a finalist’s own stadium.
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