What are the most Champions League matches were decided by penalties? Including Liverpool vs PSG in 2025

From Liverpool’s heartbreaking elimination at the hands of PSG in the 2025 Champions League Round of 16 to some of the most legendary matches in tournament history, penalty shootouts have been a defining feature of high-stakes football. Join us as we relive the most thrilling Champions League encounters that were decided from the penalty spot.

Liverpool vs. PSG (2025 Champions League Round of 16)

Liverpool’s journey in the 2025 UEFA Champions League came to an agonizing end as Paris Saint-Germain emerged victorious in a dramatic penalty shootout at Anfield. After a tightly contested two-legged affair, the aggregate score remained deadlocked, leading to extra time and ultimately a shootout that saw PSG triumph 4-1.

Gianluigi Donnarumma was the hero for the French giants, saving crucial penalties from Darwin Nuñez and Curtis Jones. On the other end, PSG’s Vithina, Gonçalo Ramos, and Ousmane Dembele calmly converted their attempts, with Warren Zaire-Emery sealing the victory. Liverpool’s Mohamed Salah was the only successful scorer for the Reds, marking an abrupt end to their European ambitions.

This result sent PSG into the quarter-finals, further establishing them as serious contenders for the title, while Liverpool faced another painful exit on penalties, recalling past heartbreaks in the competition.

Real Madrid vs. Atletico Madrid (2016 Champions League Final)

One of the most memorable penalty shootouts in Champions League history took place in the 2016 final between Real Madrid and Atletico Madrid. After a tense 1-1 draw in regulation time, extra time failed to produce a winner, leading to penalties.

Real Madrid held their nerve as Cristiano Ronaldo converted the decisive penalty, securing Los Blancos' 11th European title. Juanfran’s missed penalty for Atlético proved costly, as Zinedine Zidane’s side claimed victory in the Milan final, once again denying their city rivals the ultimate prize.

Chelsea vs. Bayern Munich (2012 Champions League Final)

Chelsea’s triumph in the 2012 Champions League final against Bayern Munich remains one of the most dramatic in history. Playing at Bayern’s Allianz Arena, the match was tied 1-1 after extra time, with Didier Drogba scoring a late equalizer for the Blues.

In the penalty shootout, Bayern took an early lead, but Petr Čech made crucial saves, including stopping Ivica Olić’s effort. Arjen Robben had earlier missed a penalty in extra time, adding to Bayern’s woes. It was Drogba who stepped up for the decisive kick, calmly slotting home to deliver Chelsea their first-ever Champions League trophy.

Manchester United vs. Chelsea (2008 Champions League Final)

The all-English final in Moscow between Manchester United and Chelsea was another unforgettable penalty showdown. After a 1-1 draw, the match proceeded to penalties, where both teams traded successful conversions.

John Terry had the chance to win it for Chelsea, but his slip on the wet turf led to a missed penalty. Edwin van der Sar then saved Nicolas Anelka’s attempt, securing United’s third Champions League title in a night of high drama.

Liverpool vs. AC Milan (2005 Champions League Final – The Miracle of Istanbul)

The 2005 final between Liverpool and AC Milan is arguably the most famous Champions League final of all time. After trailing 3-0 at halftime, Liverpool mounted an astonishing comeback to level the score 3-3, forcing extra time.

In the ensuing penalty shootout, Jerzy Dudek’s heroics, including a crucial save against Andriy Shevchenko, secured Liverpool’s fifth European crown. The victory cemented their place in footballing folklore, proving that miracles can happen on the grandest stage.

What You Need to Know About Champions League Penalty Shootouts

• Liverpool was eliminated by PSG in the 2025 Round of 16 after a 4-1 penalty shootout defeat at Anfield.
• Real Madrid won the 2016 final against Atlético Madrid via penalties, with Cristiano Ronaldo scoring the winner.
• Chelsea claimed their first Champions League title in 2012 by beating Bayern Munich in a penalty shootout at the Allianz Arena.
• Manchester United triumphed over Chelsea in the 2008 final after John Terry’s infamous slip and Edwin van der Sar’s crucial save.
• Liverpool completed an incredible comeback in the 2005 final against AC Milan before winning on penalties, in what is known as the "Miracle of Istanbul."