5 of the Biggest Upsets of the Champions League Knockout Stages

5 of the Biggest Upsets of the Champions League Knockout Stages

Isaac Darko
February 20, 2024 at 12:02 AM
In this article:
Real Madrid logo
Real Madrid
AFC Ajax logo
AFC Ajax
FC Barcelona logo
FC Barcelona
AS Roma logo
AS Roma
FC Porto logo
FC Porto
Manchester United logo
Manchester United
Manchester City logo
Manchester City
  • The Champions League has seen some big upsets over the years
  • Real shocks often come by, leaving a lasting effect
  • Here are the most shocking Champions League knockout results

Knockout football in the Champions League is widely considered the epitome of club football entertainment, featuring Europe's finest teams vying for the ultimate prize.

Throughout its history, the Champions League has been renowned for its ability to surprise, with underdog teams occasionally producing stunning upsets in the later rounds of the tournament.

Sports Brief will delve into five of the most astonishing results witnessed in the Champions League knockout stages.

Champions League's greatest shocks

Real Madrid 1-4 Ajax

Real Madrid experienced an embarrassing defeat in the Champions League knockout phase.

Despite winning the previous three editions of the tournament, Los Blancos anticipated an easy victory over Ajax, a team that hadn't won a knockout match in the competition in 22 years.

Everything seemed to be going according to plan after Real Madrid secured a 2-1 victory in the first leg in Amsterdam.

However, Erik ten Hag's squad executed a remarkable comeback at the Bernabeu, with early goals from Hakim Ziyech and David Neres flipping the score in just 18 minutes. Dusan Tadic and Lasse Schone sealed the victory, allowing Ajax to depart from Madrid with a memorable 4-1 win.

Roma 3-0 Barcelona

After clinching the trophy for the fifth time in 2015, Barcelona stumbled in the Champions League quarter-finals in the subsequent two seasons. Their fortunes seemed to change when they faced Roma in the last eight, securing a convincing 4-1 victory in the first leg at the Nou Camp.

However, just six days later, Eusebio Di Francesco's side orchestrated a remarkable turnaround at the Stadio Olimpico. Kostas Manolas' decisive header eight minutes from time propelled Roma through on away goals, leading to an electrifying commentary from Peter Drury.

The triumph marked only the second time in Roma's history that they reached the Champions League semi-finals.

Monaco 3-1 Manchester City

Manchester City under the guidance of Pep Guardiola in the 2016/17 campaign, were still a team in transition.

However, they were widely expected to dispatch AS Monaco with relative ease in the Champions League round of 16.

Yet, the French side proved formidable, boasting talents such as the 19-year-old Kylian Mbappe.

Despite City's thrilling 5-3 victory in the first leg in Manchester, they were left stunned in the return leg in southern France.

Goals from Mbappe, Fabinho, and Tiemoue Bakayoko secured a memorable win for Monaco, advancing them to the next round on away goals.

Manchester United 1-1 FC Porto

Porto's stunning victory in the 2004 Champions League, led by the promising young manager Jose Mourinho, remains one of the competition's most memorable tales.

Despite initial doubts about their chances, Porto defied expectations, especially after Benni McCarthy's two goals secured a 2-1 win in the first leg in Portugal.

In the return leg at Old Trafford, Paul Scholes' header seemed poised to send Manchester United through on away goals.

However, in a dramatic twist, United goalkeeper Tim Howard fumbled McCarthy's powerful free-kick in the dying moments, allowing Costinha to pounce on the rebound and secure Porto's spot in the quarter-finals.

Dinamo Kyiv 2-0 Real Madrid

Dynamo Kyiv owed much of their success to the formidable Andriy Shevchenko, who led their attack during his prime.

Despite this, few believed they stood a chance against reigning champions Real Madrid in the quarter-finals of the 1999 tournament.

However, the Ukrainian side held their ground, securing a 1-1 draw with Los Blancos at the Santiago Bernabeu before triumphing 2-0 in the return leg. Shevchenko scored two crucial goals in the second half.

This marked Dynamo's third appearance in the semi-finals of the competition, where they narrowly succumbed to Bayern Munich over two legs, ending their European campaign.

Isaac Darko photo
Isaac Darko
Isaac Darko is a La Liga, Ligue 1 and Bundesliga editor at Sports Brief with a Degree in Journalism and Communications from Ghana Institute of Journalism (2010)