Shock and Awe: Biggest Champions League upsets

But they just suffered one of the biggest shocks in UEFA Champions League history, eliminated by Lapland surprise-package Bodø/Glimt. How on earth did this happen? The result piqued my morbid curiosity, compelling me to catalogue some of my picks for biggest Champions League knockout upsets. I’m looking for upsets, not comebacks: Liverpool’s 2018/2019 heroics against Barcelona- as monumental as they were- don’t fit the template. These are my personal favourite shocks, where wildly underestimated sides caught more accomplished sides cold. So, in chronological order, here are six results for all those Rocky enthusiasts out there.

Real Madrid vs Dynamo Kyiv (1998/1999 quarterfinals)

Shevchenko stuns Los Blancos

This was a massive victory for not only Ukraine, but for all of Eastern European football. It also underscored the indelible impact that a certain Andriy Shevchenko had on the entire region. Shevchenko put Dynamo ahead at the Bernabeu before Mijatovic equalized. Shevchenko settled matters in the return leg in Kyiv, netting a brace to guide Dynamo to a 2-0 win (and a 3-1 aggregate win). Shevchenko opened the scoring after rebounding his own penalty miss. He then showed finesse, deftly finishing after a wonderfully waited ball from Rebrov. This was a flagship victory for Eastern European clubs in this prestigious competition (Tuesday’s night’s events at the San Siro certainly evoked the nostalgia of that moment).

Porto vs Manchester United (2003/2004 Round of 16)

The Special One lifts off

With Mourinho going on to become such an enormous success, it’s easy to forget how much of a seismic shock this result was. Porto won the first leg 2-1 (though Roy Keane’s dismissal was a huge contributor to that). But United seemed to have reasserted their superiority at Old Trafford, with Scholes firing the Red Devils into a 2nd leg lead. But Costinha would break Mancunian hearts the world over, picking up the scraps after Tim Howard failed to properly deal with Benni McCarthy’s free-kick. That goal instigated one of the Champions League’s most indelible moments, as Jose Mourinho ran down the length of Old Trafford like Usain Bolt in celebration (and to think, he would one day be embraced by those Mancunians as one of their own). In many ways, this tie gave birth to the Mourinho mystique.

AC Milan vs Deportivo La Coruna (2003/2004 quarterfinals)

2003/2004 was arguably the most chaotic year in the history of this tournament, producing a semifinal lineup of Monaco, Chelsea, Porto and- most surprisingly- Deportivo La Coruna. Javier Irureta’s side were overwhelmed in the San Siro, losing 4-1 to Ancelotti’s star-studded Milan side (this was the era of Pirlo, Kaka and Shevchenko). Deportivo incredibly wiped out the deficit in the first half of the return leg, going 3-0 up with goals from Pandiani, Valeron and Luque. Heroic captain Fran completed the rout in the 2nd stanza, making it 4-0 to seal one of the most extraordinary comebacks in Champions League history. Irureta had promised to walk the pilgrim’s trail to Santiago de Compostela ‘on his knees’ if they won. He welshed a bit on that one, opting instead to walk the distance on hiss feet.

Lyon vs APOEL (2011/2012 Round of 16)

A Cypriot fairytale story

APOEL Nicosia could have been forgiven for resting on their laurels after contriving to qualify from a group featuring Porto, Shakthar and Zenit St Petersburg. There was no way that the ragtag group of journeymen pros could go any further. Right? The Mediterranean minnows confounded all expectations, eliminating Lyon on penalties to become the first Cypriot side to qualify for the final eight of any European competition. Goalkeeper Dionisios Chiotis became a modern-day Greek god, immortalizing himself with penalty saves from Lacazette and Bastos. This was one of those jump-scare results, where you involuntarily shudder when scanning the scores of the other matches.

Ajax vs Real Madrid (2018/2019 Round of 16)

Ten Hag’s fledging Ajax do the impossible

And to think, there was a time when Erik ten Hag was considered ‘cool’, a hipster alternative to established brands like Guardiola and Ancelotti. How the mighty have fallen, but I digress. The reason this result appears on this list is because Real Madrid were crushing it in Europe during this period. Sure, this was their first season post-CR7. But they still had the likes of Benzema, Modric, Bale and Kroos. Ten Hag embraced the Dutch ethos of Total Football, heralding the arrival of an exciting batch of sought-after players (van de Beek, de Jong, de Ligt). The crazy thing about this tie was that Real won the first leg 2-1 in Holland. Ajax responded in swashbuckling style, winning 4-1 at the Nou Camp in one of Real’s most humbling home outings.

Bodø/Glimt vs Inter Milan (2025/2026 Knockout phase playoffs)

Norwegian minnows triumph in David vs Goliath clash

That brings us right back to the present moment. Frankly, I’m still struggling to believe this one. Perhaps I shouldn’t be so surprised: Bodø/Glimt did beat Man City and Atletico in the league phase. Chivu’s Inter are absolutely flying in Serie A and most people thought they would overturn that 3-1 first-leg deficit quite easily. And you can’t accuse Inter of a lack of urgency, as they enjoyed 70% possession and had a staggering 33 total shots. But they were wasteful, only managing six shots on target in a performance reeking of later-stage Inzaghi. The Norwegian outfit were clinical with the possession they did have, with Jens Peter Husgue scoring his 6th goal in what is turning out to be a glittering campaign. These are the type of moments that can leave even the most cynical viewer a bit awestruck.