The 15 best Champions League knockout games

This first round of Champions League knockout play-offs has already delivered plenty of entertainment, with some truly mammoth ties set for dramatic conclusions as the last-16 lineup is determined.

Real Madrid’s last-gasp victory over Manchester City sets up a mouth-watering tie at the Santiago Bernabeu next week, while Paris Saint-Germain are all but through after a comfortable first-leg victory over Ligue 1 rivals Stade Brest.

Elsewhere, Celtic face a daunting challenge against Bayern Munich, with Brendan Rodgers’ side hoping to pull off an upset for the ages, while Atalanta will look to continue their Champions League journey against Club Brugge.

Since the final is usually a dull affair, the knockout rounds are where all the fun is. With that in mind, we look back on 15 all-time classic knockout ties as the play-off round gets underway.

15

Borussia Dortmund 3-2 Malaga

2012/13 quarter-final

Malaga have only ever qualified for the Champions League once, where they enjoyed a shock run to the quarter-finals in 2012/13, but were ultimately bested by Borussia Dortmund.

It was close, though. The Spanish side held Dortmund to a goalless draw in the first leg before taking a 2-1 lead in the second with just minutes to go. In stoppage time, however, Dortmund scored twice through Marco Reus and Felipe Santana to book their spots in the semi-finals in dramatic fashion.

It was a bitter pill to swallow for the Spaniards, especially as Santana had looked to be offside for the eventual winner.

14

Manchester United 5-6 Real Madrid

2002/03 quarter-final

Ronaldo was the star as Real Madrid dumped Manchester United out in the quarter-finals in 2002/03. Madrid installed a commanding lead following a 3-1 victory in the first leg through goals from Luis Figo and a Raul brace.

Despite United edging a seven-goal thriller at Old Trafford, Ronaldo’s memorable hat-trick secured a 6-5 win on aggregate.

Ronaldo’s second goal, which saw him expertly control a long pass and then volley past United ‘keeper Fabien Barthez in one fluid motion, became one of the most iconic in Champions League history.

13

Manchester City 4-4 Tottenham Hotspur

2018/19 quarter-Final

The first leg of the 2018/19 quarter-final between Tottenham Hotspur and Manchester City was a narrow affair, with the Lilywhites running out as 1-0 winners in the first European game at their new stadium. The second leg, however, was a goal-fest.

City led 3-2 after just 21 minutes, before Sergio Aguero’s goal put City ahead on aggregate on the hour mark. But Fernando Llorente’s controversial goal – which saw the Spaniard bundle the ball into the net with his hip (though some may say his arm) – sent Spurs through on away goals.

In stoppage time, Raheem Sterling thought he had won it, only for VAR to rule it out for offside. An absolute modern classic.

12

Chelsea 6-5 Napoli

2011/12 round of 16

The 2011/12 last-16 tie between Chelsea and Napoli was a true tale of two ties.

Napoli dominated the first leg in Italy, winning 3-1 thanks to goals from Edinson Cavani and Ezequiel Lavezzi. With the Blues on course for an early exit and dismissing manager Andre Villas-Boas between the two legs, they produced a dramatic turnaround at Stamford Bridge.

After goals from Didier Drogba, John Terry and Frank Lampard levelled ​​​​​​the tie in regular time, Branislav Ivanovic scored the winner in extra-time to send Roberto Di Matteo’s side to the quarter-finals. We all know what happened next.

11

Bayern Munich 4-4 Man United

2009/10 quarter-final

Away goals proved decisive as Bayern Munich knocked out Manchester United in the 2009/10 quarter-finals, progressing despite a 4-4 aggregate scoreline.

Bayern snatched a first-leg victory with a late Ivica Olic winner, though were up against it as United took control at Old Trafford.

The Red Devils led 3-0 in the second leg after goals from Darron Gibson and Nani. However, Olic struck before half-time, and Arjen Robben’s stunning volley in the 74th minute secured Bayern’s passage on away goals. The Bavarians went on to lose the final against Inter in Madrid.

10

Milan 5-0 Inter

2004/05 quarter-final

Not a comeback thriller, but a drama-filled derby – Milan took the bragging rights in emphatic fashion during their 2004/05 Derby della Madonnina quarter-final against Inter.

Milan won the first leg 2-0, with Jaap Stam and Andriy Shevchenko on the scoresheet. In the return fixture, they extended their advantage with Shevchenko adding another goal before the match was abandoned in the 72nd minute due to crowd trouble, as Inter fans threw flares onto the pitch – one of which struck Milan goalkeeper Dida.

UEFA handed Milan an automatic 3-0 win on the night, making it 5-0 on aggregate.

The chaos also spawned one of the most iconic images as rivals Marco Materazzi and Rui Costa took a moment to admire the flames.

9

Roma 4-4 Barcelona

2017/18 quarter-finals

After losing 4-1 to Barcelona in the first leg of the 2017/18 quarter-finals, Roma’s chances of progressing to the last four seemed slim.

However, in front of their home fans in the second leg, they stunned the football world by winning 3-0, overturning the deficit to progress on away goals.

Edin Džeko opened the scoring in just six minutes, before Daniele De Rossi and Kostas Manolas sealed the comeback. His header was later immortalised by some iconic Peter Drury commentary.

8

Chelsea 7-5 Liverpool

2008/09 quarter-finals

Chelsea and Liverpool have seen out some classic matches over the years, but none have been quite as good as their meeting in the Champions League quarter-finals in 2008/09.

Trailing 3-1 from the first leg, Liverpool came flying out of the blocks in the return fixture at Stamford Bridge, scoring two in the first half to level the scores on aggregate.

Chelsea then scored three goals to make it 6-3, seemingly sealing the tie, but Liverpool responded with two goals in quick succession to set up a tense finish. As Liverpool pushed for an away-goals triumph, Frank Lampard scored Chelsea’s fourth, ending the Reds’ hopes of a dramatic comeback.

7

Deportivo 5-4 Milan

2003/04 quarter-finals

Milan were the heavy favourites heading into their quarter-final tie with Deportivo La Coruña in 2003/04, and things went according to the script in the first leg, with the Italians winning 4-1 at the San Siro thanks to goals from Kaka, Andriy Shevchenko and Andrea Pirlo.

However, in the second leg back in Spain, Deportivo did the unthinkable, thrashing Milan 4-0 at the Riazor. Fran’s 76th-minute strike proved to be the crucial goal that sent them into their first, and still only, Champions League semi-final.

6

Chelsea 5-4 Barcelona

2004/05 round of 16

Chelsea’s 5-4 aggregate win over Barcelona in the last-16 in 2004/05 had it all: a comeback on home soil, one of the Champions League’s greatest-ever goals, and peak Jose Mourinho dramatics.

After a 2-1 first-leg loss at Camp Nou, Chelsea stormed into a 3-0 lead in 19 minutes at Stamford Bridge, but Ronaldinho’s magical toe-poke made it 3-2, meaning the Catalans were headed for the quarter-finals.

John Terry, however, had other ideas, heading in a late winner to seal a dramatic win for the Blues, which Mourinho celebrated in a pile-on with his team while Ronaldinho and Barcelona manager Frank Rijkaard were having a scuffle with security.

5

Monaco 5-5 Real Madrid

2003/04 quarter-final

One of the biggest upsets in Champions League history, Real Madrid had looked on course for a fairly routine passage to the Champions League’s last four after beating Monaco 4-2 in the first leg of their quarter-final clash at the Santiago Bernabeu.

However, Monaco, inspired by on-loan Madrid striker Fernando Morientes, won 3-1 at home to advance on away goals, with Morientes making the difference against his parent club thanks to goals in both legs.

Ludovic Giuly netted the eventual winner, completing the three-goal comeback the French side needed after Raul’s early opener.

Monaco went on to reach the final, where they were beaten by José Mourinho’s Porto.

4

Ajax 3-3 Tottenham Hotspur

2018/19 semi-final

Tottenham’s hopes of a first Champions League final had all but vanished when Ajax had taken a 3-0 aggregate lead in their semi-final clash in 2019.

But Lucas Moura’s quickfire double had hurled them back into the tie, with a tense finale ensuing as Spurs were one away goal from advancing.

The Brazilian later wrote his name into Tottenham folklore with the latest of late goals to book their tickets to Madrid, sparking wild celebrations on the pitch and in the stands that will live long in the memory.

Unfortunately, they couldn’t quite get over the final hurdle, coming unstuck against Liverpool.

3

Real Madrid 6-5 Man City

2021/22 semi-final

Real Madrid and Manchester City went blow-for-blow in the semi-finals in 2021/22 to produce a modern-day Champions League classic.

City led 4-3 after a thrilling first leg and extended their lead in Madrid through Riyad Mahrez. In stoppage time, however, Rodrygo scored twice to force extra time, where a Karim Benzema penalty sealed Madrid’s place in the final.

Real secured their 14th European crown after overcoming Liverpool in the final in Saint-Denis.

2

Liverpool 4-3 Barcelona

2018/19 semi-finals

A tie that birthed a Liverpool cult hero, the Reds produced a remarkable turnaround to reach the Champions League final in 2018/19, beating Barcelona 4-3 on aggregate.

After a 3-0 loss in the first leg at Camp Nou, Liverpool’s hopes seemed all but dashed. However, Jurgen Klopp’s side overturned the deficit at Anfield, winning 4-0 with Divock Origi and Georginio Wijnaldum both scoring twice.

Origi’s second, a thunderous finish from Trent Alexander-Arnold’s quick corner, proved to be the decisive moment – going down as one of the most ingenious goals in the competition’s history, forever cementing Origi as a Liverpool legend.

The Reds went on to beat Tottenham 2-0 in the final, claiming their sixth European Cup, with Origi sealing the deal with a late strike.

1

Barcelona 6-5 PSG

2016/17 round of 16

Without a doubt the most thrilling comeback in Champions League history, PSG crushed Barcelona 4-0 in the first leg of their last-16 tie in 2016/17.

But in a legendary return leg at Camp Nou, Barcelona raced to a 3-0 lead. However, Edinson Cavani’s away goal meant they still needed three more to progress.

Against the odds, Neymar provided two of them, before Sergi Roberto’s 95th-minute strike sealed a historic 6-1 win. So extraordinary was the turnaround that the second leg has since been immortalised with its own nickname: “La Remontada” (“The Comeback”).