When Did Arsenal and Real Madrid Face Each Other?

This encounter was in 2006 - and featured a catalogue of some of football’s iconic names: Ronaldo Nazario, Zinedine Zidane, Roberto Carlos and Thierry Henry just to name a few.

The First English Team To Sink Los Blancos

These figures were all present for the first leg at the Santiago Bernabeu, and it was Arsenal who started brightest. Henry, Jose Antonio Reyes and Freddie Lljungberg all had opportunities to take the lead in the first ten minutes. Madrid grew into the game and forced goalkeeper Jens Lehmann – without doubt the unsung hero of the night – into four first half saves to reach the break at 0-0.

These saves then became more significant when Henry brought the game to life with a tremendous solo goal to give Arsenal their lead. The legendary Frenchman picked up possession on the halfway line, and skipped between three challenges from white shirts and last ditch tackle from Sergio Ramos, to tuck the ball into the bottom right corner.

If there is ever one criticism levelled at Henry, it was his slight reputation of not delivering in big moments. But this was a goal worthy of an all-time great, on a stage for the all-time greats, at a time when his club needed him most.

One of the great #UCL performances...

🎬 Thierry Henry vs Real Madrid, 2006 pic.twitter.com/wN6vxjef8U
— UEFA Champions League (@ChampionsLeague) June 27, 2023

“1-0 to the Arsenal” rang around the Bernabeu as they defended with their lives to leave Madrid with a one goal advantage – as the Gunners became the first English team to win at the Bernabeu.

The home leg at Highbury was equally end-to-end, but the highlight of the night was on both defences. It’s worth noting too, that Arsenal were without stalwarts Sol Campbell and Ashley Cole for these games. The Gunners’ back four of Emanuel Eboue, Kolo Toure, Phillipe Senderos and Mathieu Flamini played the game of their lives in this second leg – winning 18 out of 26 ground duels during the second leg.

A Lot Can Change In 19 Years

To this day, this encounter arguably remains Arsenal’s greatest Champions League achievement. Madrid meanwhile, have won the competition six times since.

🗣️ Thierry Henry on Arsenal’s mindset for the Real Madrid clash: “You may as well not go and play if you don't think you can beat them!” ❌🧠
pic.twitter.com/wcinE2yJE1
— DailyAFC (@DailyAFC) March 13, 2025

Yet this year’s quarter final promises to be closer than that sentence suggests. Madrid remain serial winners; an immovable object able to defy logic and chance in Europe for over a decade. For Arsenal, Bukayo Saka’s return has reinjected the feel-good factor into the club, and there is no doubt: the Gunners will be up for it at the Emirates Stadium on Tuesday.