Real Madrid in the Champions League. Six words that either send a shiver down your spine, or get your blood pumping like nothing else.  

Real are quite simply the greatest side in European history, winning a quite remarkable 15 Champions League titles, including six of the last 11. When Carlo Ancelotti’s side are in town, the world stops to take a look, and there aren’t many teams in global sport that you can say the same for. 

It is a fear-inducing prospect, but that is the gargantuan task awaiting Mikel Arteta and Arsenal in the Champions League tonight, as they take on the most successful team in the competition for the chance to reach a first semi-final in 16 years.

They became the first English side to ever beat Real Madrid at the Bernabeu, a typically unbelievable finish from Thierry Henry the only goal across both ties, as Arsenal shocked Los Blancos on the way to the final, only to lose 2-1 to Barcelona.

It was a game featuring some of the biggest names in football history, as well as a whole host of Gunners icons, and here, Mail Sport takes a look at the Arsenal XI the last time they played Los Blancos 19 years ago.  

Arsenal (4-4-1-1)

Goalkeeper: Jens Lehmann

The only goalkeeper in Premier League history to go a whole season without losing a game, Lehmann was still between the sticks for one of the Gunners greatest ever nights in European football at the age of 36. 

He retired after a brief return to the club in 2011, having left in 2008, and a cruel injury plague at the club saw him called upon to become the oldest to play for the Gunners in the Premier League, before finally retiring at the end of the season. 

He has however found the limelight since hanging up his gloves, after being caught up in several controversies in recent years. 

For example, Last year he was fined £112,500 after being found guilty of property damage and attempted fraud by a German court. Lehmann was accused of using a chainsaw to saw through the roof beams of a newly-built garage on his neighbour’s property in the summer of 2022.

He was also reportedly stopped by German police in September 2024 after enjoying Oktoberfest celebrations, with a report by Bild claiming he smelled of alcohol, and had to be taken to the police station for tests because he couldn’t complete breath tests. 

He was also on trial for dodging parking fines which are said to have since been paid. 

Right back: Emmanuel Eboue

While invincible hero Lauren was still at the club, Arsenal were forced into a makeshift defence after a spate of injuries, with Eboue on the right of a back four tasked with stopping the likes of Ronaldo, Raul, David Beckham, Guti and Zinedine Zidane. 

Eboue is a bona fide cult icon at the club, known for his colourful wristbands and energy down the right, he was even compared to Brazilian legend Garrincha by Arsene Wenger after breaking into the first team in 2006. 

After leaving for Galatasaray in 2011, he returned to England with Sunderland in 2016, before retiring in 2020. However, in 2017 he gave an interview to the Mirror in which he claimed he was struggling financially with his assets awarded to his ex-wife. 

He has also frequently opened up on his mental health struggles, particularly in dealing with the deaths of both his grandfather and his brother. 

Now, though, he has seemingly turned his life around, returning to Ivory Coast to run and own a football academy, as well as marrying his childhood sweetheart, Stephanie Boede. 

Centre back: Kolo Toure

Eboue’s international team-mate Toure was the senior figure at the heart of defence at just 25, and another graduate of that season of seasons for Arsenal fans in 2003-04. 

Known for his willingness to throw himself into a challenge and his versatility, Toure would play 326 times for the Gunners before leaving for Man City, and would also have stints with Liverpool and Celtic in a trophy-laden career. 

Since hanging up his boots in 2017, he has made a successful transition into coaching, most recently managing Wigan in the Championship, a stint that last nine games. 

Toure has now returned to former club Man City as a youth team assistant manager, having also coached Leicester and Ivory Coast. 

Centre back: Philippe Senderos

Switzerland international Senderos partnered Toure at the back after breaking into the side after an injury to Sol Campbell the previous season, and would play five knockout games for the Gunners in the Champions League campaign.

In fact, that partnership of Toure and Senderos managed to reach the final without conceding a single goal in the knockout rounds, in an astounding feat of defensive solidity.

Senderos would play 117 times for the Gunners before leaving for good in 2010, and after retiring transitioned into coaching back at his boyhood club Servette, before taking up a role at FIFA. 

Once again working under Arsene Wenger, Senderos is a ‘High Performance Specialist’ at the global governing body, and told talkSPORT last year that he aids federations in ‘develop long-term planning on talent development’.

Left back: Mathieu Flamini 

With Ashley Cole and Gael Clichy unavailable, Arsenal’s perennial utiility man Flamini was thrown into the mix at left back against the biggest, baddest bully in school in Real Madrid, but performed admirably. 

In the second leg alone Arsenal faced five shots on target and made seven blocks to stymie the Los Blancos attack, and Flamini would play all but one game in the Champions League that season, across three separate positions. 

In his two stints at the club Flamini managed 246 appearances, and while he only won three FA Cups, his greatest success has come arguably away from the pitch.

The 41-year-old, now runs a biochemical company reportedly valued close to £20billion, said to be 40 times the net worth of Cristiano Ronaldo, 40.

But Flamini insists the key to his remarkable rise from the pitch to the boardroom comes down to just three things: passion, dedication and resilience.

Speaking to The Times, he explained: ‘When I said, as a five-year-old, “I want to be a footballer”, people said, “Get your head right. It’s impossible!”

‘It’s about passion and dedication. It’s resilience. And that’s the same if you are a footballer performing in front of millions of people or an entrepreneur, or the CEO of a multinational leading 1,000 people. You have to deal with pressure, be able to inspire and to work as a team.’

Right midfield: Freddie Ljungberg  

Perhaps the greatest right winger the club have ever had, Ljungberg is somehow underrated for his exploits as one of Arsenal’s greatest ever servants. 

His 72 goals and 40 assists in 328 games for the Gunners earned him two Premier Leagues and three FA Cups, and he was twice named Sweden’s football of the year. 

Ljungberg left after nine seasons but returned back home as a coach, and even stood in as interim boss between the Unai Emery and Mikel Arteta eras, and after dropping into the latter’s senior coaching staff he left the club before the start of the 2020-21 campaign.

Now, Ljungberg has joined back up with Lehmann and Robert Pires in the Baller League, with the trio of Arsenal icons running N5 FC.

Central midfield: Cesc Fabregas

One of the most technically gifted players to ever wear an Arsenal shirt, future World Cup and European Championship winner Fabregas faced off against a number of his fellow Spain internationals on that night in 2006. 

Given the captain’s armband in 2008 at just 21, he flourished for the Gunners before returning home to Barcelona in 2011, later having spells at Chelsea, Monaco and Como. 

Now 37, he only retired in July 2023, and has proven himself to be a very capable coach at the highest level of the game. 

After standing in for a month last season, Fabregas was named Como’s head coach for their return to Serie A, and has remarkably guided them to mid-table, with the Italian side 13th and nine points above the relegation spots. 

Central midfield: Gilberto Silva

Another criminally underrated Gunners icon, Gilberto was a crucial part of the Invincible machine, and remained central to Arsenal’s plans until his departure in 2008. 

A World Cup winner with Brazil, Gilberto returned to his home country later in his career, before officially retiring in 2015. 

After hanging up his boots the midfielder took on ambassadorial roles with both Arsenal and FIFA, and featured on an expert panel during the 2022 World Cup as part of the BBC’s coverage. 

Left midfield: Aleksandr Hleb 

Belarus’ most notably footballing export, Hleb played 130 times for the Gunners and scored 20 goals before his departure for Barcelona in 2008, something he later admitted was the biggest regret of his career. 

After things didn’t quite go to plan for him at the Nou Camp, he embarked on a legendary journeyman career that saw him bring his total number of senior stints at Belarusian giants BATE Borisov up to five. 

Hleb had stints in coaching and even in front of the camera, as well as reportedly studying for a law degree after hanging up his boots five years ago. 

Second-striker: Jose Antonio Reyes 

Playing just in behind the striker on that fateful night was Spanish international Reyes, who was actually loaned out to Real in the summer of that same year and scored the goals against Mallorca that confirmed their status as LaLiga champions in 2006-07. 

Reyes played 110 times in total for the Gunners, scoring 23 goals and providing 27 assists before his departure for his home country, and would later win three Europa Leagues with Sevilla, to add to two won with Atletico Madrid. 

Tragically, though, Reyes was killed in a car accident in 2019 at just 35 years of age. 

The footballer was killed along with his 23-year-old cousin while another man suffered serious burns when the vehicle they were travelling in overturned and burst into flames in Utrera, the town where Reyes was born, just outside Seville.

He was reportedly on his way home to his wife and three children after training when the accident occurred. His coffin was carried through the streets of his hometown, Utrera, and was draped in a Sevilla flag, with then-Arsenal boss Unai Emery in attendance. 

Striker: Thierry Henry 

Naturally, Henry was the difference-maker in the tie against Real Madrid, as he was for practically his entire career. 

The best forward in the history of the Premier League, Henry is Arsenal’s record goal scorer with 228 in 377 games, and they don’t come much better than his masterpiece in the Spanish capital.

He stunned the Bernabeu in an awesome display in the first leg, silencing the home crowd after wriggling through four challenges to convert past Spanish icon Iker Casillas and ultimately win the tie for the Gunners. 

He later joined Real’s arch rivals in Barcelona, where he won a Champions League, two LaLiga titles, a Copa del Rey, Spanish Supercopa, UEFA Super Cup and Club World Cup under Pep Guardiola, before moving to the New York Red Bulls. 

There would be a gilt-edged return to Arsenal in the off-season in the US as well, which yielded two goals back in 2012.  

In retirement, Henry has coached at youth and senior level, taking charge of Monaco for 20 games, and MLS side Montreal Impact, was assistant to Roberto Martinez at Belgium, and took France’s U21s to the Olympic Games final. 

He has also become a renowned pundit, having worked at Sky Sports, Amazon Prime Video and CBS Sports Golazo, where he joins Kate Scott, Jamie Carragher and Micah Richards as part of the presenting team. 

Real Madrid

The Real Madrid team on that night featured some of the biggest names the game has ever seen, and so it would be remiss not to mention just a few of those living legends. 

Up front was Ronaldo Nazario, considered by many to be the greatest No 9 of all time, and just in behind the Brazilian Ballon d’Or winner was Raul Gonzalez, who at one point simultaneously held the records of Real Madrid’s all-time top scorer, Spain’s record goal scorer and the Champions League’s top scorer. Quite the pairing. 

Then if that wasn’t enough, the midfield included another Ballon d’Or winner in Zinedine Zidane, arguably England’s best ever player in David Beckham and three-time Champions League winner Guti, who racked up an astonishing 542 games for Real. 

The defence saw Roberto Carlos wearing the No 3 shirt, and there aren’t many to have every played the game better than him in that role, with Sergio Ramos – who would win two European Championships and a World Cup with Spain – at centre back. 

It’s perhaps no surprise Arsenal only made one breakthrough across both legs considering that even when they did get through all that ridiculous talent, there was still Iker Casillas to beat, regarded as one of the very best to ever wear the gloves in the history of the game. 

In all, it was an unprecedented win for the Gunners all those years ago, but now attention turns to Tuesday night’s first leg, and the chance to do something equally special for Arteta and Co. 

Beat Real across both legs this time round, and not only will they have a spot in the last-four of the Champions League for the first time in 16 years, but they’ll also make it two wins in two over Real Madrid, a rare achievement if ever there was one.