Ranking Arsenal’s 11 greatest European games after knocking out Real Madrid

Arsenal are preparing for a first Champions League semi-final since 2009 after defeating defending European champions Real Madrid.

The Gunners were 3-0 up from the first leg thanks to Declan Rice’s double and Mikel Merino’s strike, and sensationally won 2-1 at the Bernabeu after a late winner from Gabriel Martinelli.

Their reward is a tie against Paris Saint-Germain, with the winner heading to Munich to face either Barcelona or Inter.

The last week or so has seen Arsenal add to their prestigious list of memorable European nights, with their first-leg victory over Los Blancos arguably the greatest night the Emirates Stadium has ever seen.

With that in mind, here is a look at the best European matches in the club’s illustrious history.

11

Roma 1-0 Arsenal (6-7 on penalties)

2008/09 Champions League, round of 16 second leg

After securing a 1-0 win at home, Arsenal went to Rome’s Stadio Olimpico in 2009 hoping to finish the job without any major issues.

However, the Gunners fell behind pretty quickly, with Juan levelling the aggregate scoreline inside 10 minutes.

With no further goals on the night, a shootout was required, and despite Eduardo’s miss for the visitors, Manuel Almunia saved from Mirko Vucinic and Max Tonetto blazed over to send Arsene Wenger’s side through to the last eight.

10

Arsenal 2-0 Juventus

2005/06 Champions League, quarter-final first leg

Arsenal delivered one of their finest results in the Champions League when seeing off Juventus in the first leg of their quarter-final in 2006.

Buoyed by eliminating Real Madrid in the previous round, the home side went ahead through Cesc Fabregas, who slotted past Gianluigi Buffon just before the break.

Thierry Henry then scored against his former club to double Arsenal’s advantage and cap a magical night at Highbury, with the Old Lady held to a goalless draw in the second leg in Turin.

9

Arsenal 3-0 Anderlecht

1969/70 Fairs Cup, final second leg

It feels strange to put a final so low on this list, but 55 years on, Arsenal’s victory against Anderlecht in the Inter-Cities Fairs Cup to secure their first European trophy would be worth a mention in any case.

Down 3-1 from the first leg, Ray Kennedy’s consolation in Belgium would set up a superb comeback at Highbury.

Eddie Kelly got the ball rolling in north London, before two goals in two minutes from John Radford and Jon Sammels handed the Gunners the trophy.

Bertie Mee’s side would go on to win the league and cup double the following season.

8

Arsenal 1-0 Porto (4-2 on penalties)

2023/24 Champions League, round of 16 second leg

Arsenal had been out of the Champions League for six seasons before their long-awaited return in 2023/24, with their wait for a quarter-final stretching back to 2010.

So when they went 1-0 down late on against Porto in the first leg, history looked like repeating itself, with Arsenal’s last seven Champions League campaigns ending at the last-16 stage.

Leandro Trossard put Mikel Arteta’s side in front on the night, but there were no more goals on a tense night in north London.

Thankfully, the Gunners were faultless from the spot, with David Raya’s save from first-leg hero Galeno sparking wild celebrations at the Emirates.

7

Milan 0-2 Arsenal

2007/08 Champions League, round of 16 second leg

Arsenal were underdogs heading into their clash in the San Siro to face reigning European champions Milan, but came away with one of their best results on the road in Europe.

A goalless draw at the Emirates meant a score draw would be enough to send the Gunners through without the need for extra time, but if anything, it looked as though another 0-0 was on its way.

Six minutes from time, Cesc Fabregas picked the ball up in the centre of the field and unleashed a shot from 30 yards, which somehow found the corner to all but seal the result for Arsenal.

Emmanuel Adebayor scored late on to put the icing on the cake.

6

Inter 1-5 Arsenal

2003/04 Champions League, group stage

Rather incredibly, Arsenal’s heroics against Milan may not even be their greatest in the San Siro.

While their victory over Inter was only in the 2003/04 group stage, it probably trumps their win over the Rossoneri for the fact that a win was vital, and that the scoreline remains stunning to this day.

Arsenal had a horrendous start to their group campaign, earning one point from their first three matches, and required a win in Milan to stay alive.

That meant beating a team that had thumped them 3-0 at Highbury just two months earlier.

Fortunately, Thierry Henry was in red-hot form, and hit a brace to help smash an Inter side that fell apart in the second half, with Freddie Ljungberg, Edu and Robert Pires all getting in on the act before the final whistle as Arsenal smashed their opponents on their way to winning Group B.

5

Arsenal 1-0 Parma

1993/94 Cup Winners’ Cup final

Arsenal’s most recent European trophy was secured 31 years ago, when an unfancied Gunners side saw off favourites Parma in the Cup Winners’ Cup final in Copenhagen.

George Graham’s side, who were also without the suspended Ian Wright, took a surprise lead through Alan Smith’s volley in the first half.

Parma’s stars, including Gianfranco Zola, Faustino Asprilla and Tomas Brolin, had plenty of chances either side of Smith’s effort, but the defence remained resolute to bring the trophy home.

4

Villarreal 0-0 Arsenal

2005/06 Champions League, semi-final second leg

Arsenal were 90 minutes away from their first Champions League final after a 1-0 success in Highbury’s final European game against Villarreal.

The surprise package in the Champions League that season, Villarreal were hoping to overturn their deficit to set up an all-Spanish affair in the Paris finale.

And just when Arsenal looked like seeing it out, the hosts were awarded a soft penalty in the final moments, with extra time now looking like a certainty.

But Jens Lehmann had other ideas, diving to his left to keep Juan Roman Riquelme’s spot-kick out and send the Gunners through.

3

Arsenal 2-1 Barcelona

2010/11 Champions League, round of 16 first leg

While this tie eventually ended in controversial defeat, the first leg of Arsenal and Barcelona’s last-16 tie in February 2011 can still give fans goosebumps.

Led by Pep Guardiola, tournament favourites Barca took the lead through David Villa’s first-half finish, only for a late Gunners comeback to send the visitors home defeated.

Robin van Persie levelled an absorbing tie after catching out Victor Valdes at his near post, before an incisive breakaway saw Samir Nasri find Andrey Arshavin free in the box to slam home the winner.

2

Arsenal 3-0 Real Madrid

2024/25 Champions League, quarter-final first leg

Mikel Arteta’s Arsenal came of age when they came up against the European champions at the Emirates Stadium, with a second-half blitz seemingly putting the tie beyond their opponents.

A close tie exploded into life in the second half when Declan Rice curved a superb free-kick around the Madrid wall to draw first blood, before repeating the trick with an arguably better strike just minutes later.

Makeshift striker Mikel Merino then rounded off a super move to give Arsenal a golden chance of defeating their fancied opponents and make the semis for the first time in 16 years – a chance they didn’t pass up.

1

Real Madrid 0-1 Arsenal

2005/06 Champions League, round of 16 first leg

Winning at the Bernabeu is difficult enough, but for Arsenal to do so without several key players and while in indifferent form, it is tricky to say that their win over Real Madrid in 2006 isn’t their most impressive achievement thus far.

Arsenal came firing out of the blocks in Madrid, taking the game to their opponents and eventually getting their reward moments into the second half, with Thierry Henry racing clear of the defence to finish past Iker Casillas.

The second leg, where Arsenal held Los Blancos to a goalless draw, was just as heroic, but after becoming the first English team to win on Real’s home ground with an under-strength side, there has arguably been no greater feat than their 1-0 success against the Galacticos.