Arsenal's continued quest for a long-awaited first UEFA Champions League title faces the toughest of challenges in the quarter-final when they take on Real Madrid.
The La Liga giants have lifted the trophy a record 15 times, including last season, and will have the benefit of playing the second leg of the tie at home, a match which can be seen live on TNT Sports and
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Even ahead of the first leg at Emirates Stadium, injuries, inconsistent form and just general Real Madrid Champions League 'aura' all place Mikel Arteta's side as firm underdogs as far as progression to the final four is concerned.
However, this was also very much the case when Arsene Wenger took his side to the Bernabeu in the competition round of 16 back in 2006.
On February 21, Arsenal were supposed to be lambs to the Galactico slaughter, but a strong defensive display - with a make-shift backline, no less - kept the likes of Zinedine Zidane, David Beckham and Ronaldo quiet.
At the other end, Thierry Henry showed exactly why he was considered one of the sport's GOATs with a sensational solo goal to seal a famous 1-0 win to take back to Highbury.
Two weeks later, that stubborn Arsenal defence were at it again to seal safe passage to the next round in an uncharacteristically thrilling 0-0 draw.
The win in Spain remains one of the most memorable in Arsenal's European history and provided a platform for wins over Juventus and Villarreal as they reached the final in Paris, but were unfortunately beaten by Real's arch rivals Barcelona.
Here we look back on how the two teams lined up that day, and what happened next:
Real Madrid XI
Iker Casillas - Goalkeeper
Real’s number one would rack up 725 appearances for the club by the time of his departure in 2015, the second most of any player in the club’s history.
Lifted a long-awaited third Champions League crown in 2014 before heading to Porto 12 months later, where he helped the club to the 2018 Primeira Liga title, in addition to two European Championships and a World Cup with Spain.
Casillas suffered a heart attack in 2019, which ultimately led to him retiring a year later, and he currently works as a TV pundit in Spain.
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Cicinho - Right back
The Brazilian defender had only recently joined the club, but an ACL injury at the start of the following season ultimately saw him lose his place in the side.
A move to AS Roma followed, which included loans to Sao Paulo and Villarreal before leaving Italy in 2012 and ending his career with spells at Sport Recife and Sivasspor. The defender also earned 15 caps for his country.
Sergio Ramos - Centre back
After 16 years, 671 appearances, five La Liga titles and four Champions Leagues, some vital goals, and TWENTY-FOUR red cards, Ramos left Real Madrid for Paris Saint-Germain in 2021.
Two years later, he made an emotional return to hometown club Sevilla for a season and currently turns out for Monterrey, having joined the Mexican side in February 2025.
He also starred for Spain’s golden generation, winning two European Championships and a World Cup.
Johnathan Woodgate - Centre back
Perhaps unfairly, Woodgate’s time at Madrid is often remembered for his debut when he scored an own goal and was sent off against Athletic Club.
Although things picked up as he established himself in the first team, injuries impacted his time in Spain, leading to a loan, then a permanent move to hometown club Middlesbrough in 2006.
The England defender joined Tottenham in 2008 and scored the winning goal in the League Cup final within weeks of his arrival, but injuries again saw him eventually move to Stoke before a return to Middlesbrough and retirement in 2016.
A move into coaching eventually led to him managing the club, before taking charge of Bournemouth, but he has since returned to Boro as a first-team coach under Michael Carrick.
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Roberto Carlos - Left back
Having been at the club for the best part of a decade, the explosive Brazilian left-back left Spain for Fenerbahce a year later, followed by spells with Corinthians and Anzhi Makhachkala before retiring.
He briefly managed the Russian club on an interim basis before taking charge at Sivasspor, Akhisarspor and had a player-manager stint with Delhi Dynamos.
Thomas Gravesen - Centre midfield
The tenacious Dane only spent a season in Spain, finding himself leaving the club following a training group scrap with team-mate Robinho ahead of the next season.
Celtic called, and Gravesen moved to Scotland but went back on loan to former club Everton in 2007 before retiring in 2009, aged just 32, reportedly moving to Las Vegas, winning a fortune at Poker and living next to Hollywood A-listers.
David Beckham - Right midfield
The England star called time on his Madrid career in 2007, moving to LA Galaxy in MLS.
A loan move to AC Milan and a short stay at PSG in 2013 brought the curtain down on his playing career.
For England, Beckham captained his country at the 2006 World Cup and finally ended his Three Lions career in 2009.
Post-playing, Beckham bought a stake in Salford City with his ex-Manchester United team-mates, and now also owns MLS side Inter Miami.
David Beckham and Gilberto Silva
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Guti - Centre midfield
The dictionary definition of a stalwart of this Real team, Guti ended a 25-year association with the club in 2010, moving to Besiktas for a year before retiring in 2012.
A move into coaching saw him returning to the Bernabeu as a youth coach before an assistant role at Besiktas and a head coach job at Almeria until 2020.
Zinedine Zidane - Centre midfield
This would be Zidane’s final season as a player, winding up his career for France at the 2006 World Cup with typically brilliant displays throughout the tournament, but bowing out in the most infamous manner imaginable; headbutting Italy’s Marco Materazzi in the final and getting sent off as Les Bleus were beaten on penalties.
Returning to Madrid in more behind-the-scenes roles, Zidane took charge of the club’s B team in 2014 before getting the big job in January 2016, and winning the UEFA Champions League just months into his tenure.
With Zidane at the helm, Real completed an incredible ‘three-peat’ in the competition over the next two seasons before he stepped down in 2018.
Less than a year later, he was back in the Bernabeu dugout but could not repeat his earlier heroics in Europe, although he added a second La Liga title after one collected during his first spell.
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Robinho - Left wing
Left Madrid for Man City in 2008 as the club’s first major signing by the Abu Dhabi United Group following their takeover of the club, but joined AC Milan in 2010 before spells at Guangzhou Evergrande, Atletico Mineiro, Sivasspor, Istanbul Basaksehir, and first club Santos.
He is currently serving a nine-year prison sentence after being convicted of rape.
Ronaldo - Striker
Despite a total of 104 goals by the time he left Real Madrid after four and a half years in 2007, O Fenomeno was suffering more and more injuries at this stage of his career, which impacted his next move to AC Milan, limiting his playing time at San Siro.
Returning to Brazil after another lengthy layoff in 2009, he would score 35 goals in all competitions for Corinthians over two seasons before finally hanging up his boots.
In 2018, he moved into club ownership with the purchase of shares in Spanish side Real Valladolid.
Subs: David Cobeno, Michel Salgado, Raul, Julio Baptista, Antonio Cassano, Carlos Diogo, Alvaro MejIa.
Manager: Juan Ramon Lopez Caro - Having been in charge of Real Madrid B since 2001, Caro was installed as first team manager just three months before the Arsenal clash, replacing Vanderlei Luxemburgo.
The European exit and finishing a distant second to Barcelona in La Liga saw him leave the club in the summer.
He took over at Racing Santander but left within a month without taking charge of a single match, joining Levante, then Celta, Spain under-21s, Vaslui in Romania, Saudi Arabia, Oman and then Dalian Yifang and Shenzhen in China.
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Arsenal XI
Jens Lehmann - Goalkeeper
The German stopper was in the middle of a record-setting match run of eight consecutive clean sheets in the competition, but after denying Real, he came unstuck in the final against Barcelona with a red card in the first half of the eventual 2-1 defeat for The Gunners.
He remained with the club until 2008, when he left for Stuttgart and retired in 2010 before a brief return to Arsenal in 2011 amid a goalkeeping injury crisis.
Lehmann was also number one for Germany at the 2006 World Cup and Euro 2008, helping his country reach the semi-final and finals of those respective competitions.
Emmanuel Eboue - Right back
The Champions League run helped the Ivorian establish his place in the first team, replacing the increasingly injured Lauren at right back going forward.
He was often deployed in a right midfield position later on with mixed results. He left for Galatasaray in 2011, winning two Super Lig titles, before attempting a return to the Premier League with Sunderland in 2016, but never played for The Black Cats after receiving a ban over unpaid agent fees.
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Kolo Toure - Centre back
After his Bernabeu heroics, Toure tortured another Spanish club with what proved to be the winning goal against Villarreal in the semi-finals.
Toure left Arsenal in 2009 for Manchester City, winning a second Premier League title in 2012 to add to his 2004 medal with The Gunners, and after joining Liverpool in 2013, narrowly missed out on a potential record third crown with three different clubs.
He did add to his haul with the Scottish League title in 2017 when he moved to Celtic before retiring and moving into coaching with The Hoops, Leicester, and a brief spell as manager of Wigan.
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Philippe Senderos - Centre back
The Swiss defender failed to nail down a first-team place at Arsenal and had brief loan spells with AC Milan and Everton before joining Fulham on a permanent deal in 2010.
He then joined Valencia, Aston Villa, Grasshoppers, Rangers, Houston Dynamo and Chiasso before retiring in 2019.
Senderos also played for Switzerland at three World Cups and a European Championship, and became sporting director at Servette after hanging up his boots.
Currently working for FIFA as a high-performance specialist.
Mathieu Flamini- Left back
Flamini slotted in as a makeshift left back during the run, and became a key player in his more familiar midfield role in future seasons before a move to AC Milan in 2008, featuring in their 2011 Scudetto-winning side.
He returned to Arsenal in 2013 before spells at Crystal Palace and Getafe.
Since retiring, he has made headlines for founding GFBiochemicals, leading to wild speculation that the venture has made him a multi-billionaire.
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Freddie Ljungberg - Right midfield
Another of Wenger’s Invincibles, Ljungberg left the Emirates in 2007 for West Ham and later played for Seattle Sounders, Chicago Fire, Celtic, Shimizu S-Pulse and Mumbai City.
Ljungberg returned to Arsenal as an academy coach and, after working as an assistant at Wolfsburg, was back working in north London, even briefly taking charge as interim boss after Unai Emery was sacked in 2019.
Alexander Hleb - Left midfield
The tricky Belarusian winger moved to Barcelona in 2008 but struggled to impose himself at Camp Nou, going on loan to former club Stuttgart, Birmingham and Wolfsburg before a permanent departure to Krylia Sovetov and a somewhat nomadic end to his career, with spells at BATE Borisov, Konyaspor, Genclerburligi and Isloch Minsk Raion.
Gilberto Silva - Centre midfield
The Brazilian midfielder left the club in 2008, having been passed over for club captaincy in favour of William Gallas, joining Panathinaikos and helping the club to the Greek title and cup double in 2010.
He eventually returned to his home country for spells with Gremio and Atletico Mineiro, with whom he won the Copa Libertadores in 2013 before his retirement.
Philippe Senderos and Ronaldo
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Cesc Fabregas - Centre midfield
Fabregas would become Arsenal’s main man in the coming years, with Wenger even handing him the captain’s armband in 2009.
However, the lure of a move "home" to Barcelona proved too much in 2011, and there was a huge shock in 2014 when he returned to the Premier League with London rivals Chelsea.
He would win two league titles with The Blues before moving to Monaco in 2019 and then Como, where he currently remains in his first managerial role.
Jose Antonio Reyes - Second striker
The one-time Gunners record signing actually joined Real on loan that summer and scored the decisive La Liga winning goals against Mallorca on the final day of the 2006/07 season.
Bizarrely, he then signed for cross-town rivals Atletico just weeks after that title win and joined Benfica on loan a year later. He then returned to his first club Sevilla, winning three UEFA Europa League titles, before spells at Espanyol, Cordoba, Xinjiang in China, and Extremadura.
Reyes was tragically killed in a car accident on June 1 2019.
Thierry Henry - Striker
Henry would go on to become Arsenal’s all-time top goalscorer with 228 goals in all competitions, winning four Premier League Golden Boot awards and two European Golden Shoe crowns.
His match-winning performance at the Bernabeu proved a taster for Spanish audiences as he joined Barcelona in 2007, helping Madrid’s rivals to a historic treble-winning campaign in 2008/09.
A move to New York Red Bulls followed in 2010, before a short but memorable loan return to Arsenal at the start of 2012 during the MLS off-season saw Henry add to his Gunners tally of goals – including a winner on his second debut against Leeds United in the FA Cup.
He moved into coaching after his 2014 retirement, working with the Arsenal academy, twice being an assistant with the Belgium national team, as well as roles at Monaco and Montreal Impact.
Thierry Henry celebrates at the Bernabeu in 2006.
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Most recently, he took the French Olympic football side to the men’s tournament final at Paris 2024.
Subs: Manuel Almunia, Abou Diaby, Robert Pires, Alex Song, Theo Walcott, Johan Djourou, Arturo Lupoli
Manager: Arsene Wenger - The Frenchman would lead The Gunners to the final, where they were beaten by Barcelona in Paris and remained at the club until 2018, winning three FA Cups in that period.
After leaving the club following 22 years in north London, Arsenal's most successful manager took on a role at FIFA where he currently works as Chief of Global Football Development.
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