These observations — where I look at Real Madrid’s history, its players on loan, Castilla, tactical tidbits, and other relevant thoughts -- are now a regular thing. All previous editions can be found here.
Even with the amount of content we churn out on a daily basis at Managing Madrid, we don’t hit on nearly as much history as I’d like. Sure, we sprinkle in as much as we can through podcasts, and this particular episode will never die — but there’s always more. In fact, we could’ve dragged that episode out for another nine hours and still just be getting started. Realizing how vast the details on this club are, past and present — tactics, squad management, front office moves and all — is what stemmed me to write my upcoming book ‘The Holy Book of Madridismo’. But that won’t be out for a long time, and just to take a break from writing the book (and unplug from the current state of affairs) I decided to revisit some memorable moments — good and bad — that I experienced as a Madridista between 1999 - 2009.
Let me gloss over the criteria for this incoming list for your convenience: There is no criteria.
This is you, living vicariously through me, through moments that stuck with me and will continue to stick with me until my heart stops beating. This is not a list of ‘best moments / goals / assists’ etc. It includes a lot of nostalgia and trauma.
The timeline I chose for this project, 1999 - 2009, has its purpose. A lot of our fans are new, joining us from the atomic summer in ‘09. This we know, mostly because of our experience reading incoming mail from fans daily, as well as the comments on our site and social media. These fans continually ask for more details on important moments prior (hence why I wrote this article on Raul, to help fans who weren’t around at the turn of the century to feel more connected to one of the most important players in club history), so we often refer to historical details on our podcasts. But I won’t go back before 1999 for this particular piece. My personal football journey began in the ‘97 - ‘98 season, when Real Madrid won la Septima. But I was too young to really be a fan besides just watching football alongside my father. I started to really get into football emotionally during World Cup 98; then I became really invested in club football for the first time in the ‘98 - ‘99 season.
Since, I’ve gone back and watched full matches from the Di Stefano era (and beyond) for my upcoming book — but watching those games in hindsight doesn’t bring you the same feeling as watching live, for obvious reasons.
1999 - 2009. Let’s go.
(None of these are in chronological order.)
The Bayern Brawl: March 10, 2004
The 2003 - 2004 season was officially the dawn of the ‘dark era’, where the club ensued a number of mediocre years and a ton of coaches which Real Madrid flipped through like a scrapbook. Shortly after eliminating Bayern in the round-of-16, Real were knocked out by Monaco in the quarter-finals, and didn’t become quarter-finalists again until 2011.
The team scraped through Bayern at the Bernabeu to win 2 - 1 on aggregate. Towards the end of that tight contest, Bixente Lizarazu and Guti got heated, and pretty well everyone got involved. This is the best footage I could find:
The background here: Real Madrid were hounding Bayern furiously to end the game. It started with a throw-in for the Germans high up the left flank, where Schweinsteiger and Ze Roberto were trying to find some space to get a cross in. They were met by a demon-possessed Beckham, Cambiasso, and Salgado — just digging as deep as possible to dispossess Bayern aggressively. Demichelis came over to support the play, and once he got the ball, Guti came over to double-team him with Salgado. They ended up kicking away at Demichelis — getting the ball but also hacking away at his legs while he was on the ground. And that’s where it exploded, with Lizarazu getting in Guti’s face.
Maybe I don’t remember it if Kuffour doesn’t push Raul into Guti — with Guti hitting the deck hard. But that ridiculous moment capped the ridiculousness of it all — and it made the victory that much sweeter.
(Side note: be grateful for the Ramos - Varane era. That was Alvaro Mejia you saw in the above video — a man who totally broke down against Monaco in the next stage. Real Madrid’s central-defender situation post peak-Hierro was really bad until Pepe came along and Ramos grew into his CB role.)
Luis Figo’s haunting penalty miss: May 14, 2003
Since 1999, only one moment broke my heart more than Figo’s penalty miss in Turin: The heart-wrenching, penalty-shootout elimination against Bayern Munich in 2012 at the Bernabeu.
Most of you have heard me relive these top-two traumatizing moments. And if we’re being clear, most of you don’t need me to relive them for you — because you experienced the pain yourselves. 2012 was extra traumatic because that was supposed be our year. We had waited too long (relative to the spoiled Real Madrid fans that we are) for la Decima, had been leading in the match by two goals before letting Bayern back in the game, had watched Higuain annoyingly keep himself offside in what would’ve been a breakaway at the end of extra-time, had a less-than-potent Chelsea waiting for us in the final, and on top of that, we lost in a fucking penalty shootout in front of our own fans. Too cruel.
Growing up supporting this team, the 2003 exit was almost as bad. It was a bitter exit for mostly one reason: It was the best year of that galactio era, and it came up empty in Europe. It was the year before the team had (not directly, but essentially) replaced Beckham with Makelele. Zidane, Figo, Raul, and Roberto Carlos were all still at a very high level. Ivan Helguera was in his peak. Makelele was a wall defensively to mask defensive frailties. OG Ronaldo had just come off a hat-trick in Old Trafford. Waiting for us in the final: An absolutely brilliant AC Milan side. It would’ve been a historic final between two incredible European giants at the peak of their powers.
As the second leg unfolded in Turin, it was clear that everything that was supposed to go wrong, did. Claude Makelele, the essential keystone, could not play due to injury. It’s not just that Makelele was insanely important, but you needed him that night in Turin in particular, against a team that was tactically exemplary; against a team you needed to defend a slim lead against; against a team that wanted to spoil Zidane’s comeback party; against a team that boasted Zidane’s successor in Nedved, who was in the process of proving a point; and against a team that played in a country you historically crumbled in — over and over again.
Furthermore, Ronaldo, who later came in and caused a bunch of discomfort for Juve’s backline, nearly scoring twice, including a last second chance that would’ve saved Real Madrid’s European season (and as the possessed Del Piero put it: “(there was) much suffering in the closing minutes”) couldn’t start because of a niggling injury. Del Piero was roasting Salgado and Hierro in this game, and Juventus’s scheme caused Raul to be isolated and disconnected from the rest of the team. It was hard for Real Madrid to find openings until Ronaldo came in, and his first contribution as a substitute was to win a penalty and give Real Madrid a life-line.
I remember thinking when it happened ‘ahh shit, we got this now! No way Figo misses this. He’s reliable from the spot, always. No way he pick THIS MOMENT to launch one of the worst penalties of his career’. But, he kicked a tame penalty at Buffon, and at the same time kicked a dagger into my heart.
Here’s the two-minute highlight reel from that match, in case you enjoy sadism, or enjoy seeing Hierro playing long after he should’ve stopped playing football:
Real Madrid 3 - 2 Lazio: December 6 2001
There is no real particular significance to this game from a historical perspective. It was a mere group stage fixture (in the second of two group stage phases in the Champions League at the time). But it has its nostalgic place in this wonky list of mine.
This game was pure hype. Lazio, at the time, were a powerhouse. They were one of Europe’s biggest teams (even if they underachieved), with a ridiculous roster: Angelo Peruzzi, Sinisa Mihajlovic, Alessandro Nesta, Diego Simeone, Pavel Nedved, Juan Veron, Marcelo Salas, and Hernan Cresp (among a lot of solid guys around them like Claudio Lopez, Fabrizio Ravanelli, Simone Inazghi, Ivan De La Peña, Lucas Castroman, Dejan Stankovic, Dino Baggio, Karel Poborsky, Giuseppe Favalli, and Fernando Couto — squad was deep as hell).
Reasons why that particular match sticks out, and embodies the team that year, is as follows:
- Peak Figo. Unstoppable. Did whatever he wanted on the right flank and did it whenever he wanted to. People who didn’t watch him play regularly or only caught him later in his career don’t still quite understand what I mean when I say: He dribbled past people at will.
- On the opposite flank was Steve McManaman, who, instead of being pushed out of the club upon Figo’s arrival, was pushed to the left flank where he was highly efficient and contributed to the beautiful football the team played that year.
- The Makelele - Helguera double-pivot, which was severely underrated, mostly because Helguera was underrated. Ivan was at his best as a defensive / central midfielder, whereas most people remember him as an average central defender. Helguera could play as a box-to-box midfielder. His performances there was a real reason why a lot of fans didn’t want to sign Patrick Vieira at the time. Helguera had an amazing knack for arriving in the box to get on the end of crosses — sliding in for a low tap-in or being an aerial presence — and could also shoot from range. Him and Makelele together provided much needed balance to the team and allowed Real Madrid to control a lot of possession.
- The Raul and Morientes duo was still around for us to enjoy.
- The team played really nice football that year. There was a lot of movement in the final third and it was never stagnant, and rarely unimaginative. In this particular match, Real Madrid had 62% possession and outshot Lazio 29 - 9.
- Pedro Munitis — so much fun off the bench.
- Iker Casillas struggling with crosses (hey — I didn’t say all memories were good).
- Drama! A penalty from Figo at the death to bag the three points and put Real Madrid comfortably at the top of the group.
Sorry for the footage quality:
Dat build-up: April 23, 2003
My favourite build-up goal from that era. Ronaldo’s second goal at Old Trafford:
Asi, asi, asi gana el Madrid
Steve McManaman’s slingshots: Eternal
Few things in life are more aesthetically pleasing than Steve McManaman’s volleys where he uses his left analog stick to aim, and his right analog stick + power button to conjure the perfectly weighted, alien-like missile that you should only be able to see in an anime soccer flick with Dragon Ball characters:
Selling Esteban Cambiasso: Summer of 2004
Claude Makelele is the obvious ‘what on earth were we thinking selling him and mortgaging the next half-a-decade’ transfer blunder — but that’s too mainstream for this list, and we need a more hipster blunder to rant about.
Selling Makelele was a mistake — a stain on Florentino’s legacy. We live and die with Florentino’s incredible vision and overall overwhelmingly great tenure and decision-making. But selling Makelele (along with a list of clear mistakes, and some others that were debatable) was something that set the club back years. Maybe Makelele solves everything if he doesn’t refuse to play for the club and threaten Florentino with ultimatums — or telling Raul that Real Madrid shouldn’t count on him as he’s only in training to stay fit while he pushes his way to Chelsea. Maybe Makelele should’ve seen out his contract. But maybe he was one of the greatest defensive midfielders of all time, and that grants you a raise.
But there needs to be a place for Cambiasso in the museum of Real Madrid ‘what ifs’. Maybe we sold Makelele in part due to getting irrationally confident that we got lucky with the Redondo sale, where we somehow fluked into stumbling onto Makelele being better than we thought he would be after signing him from Celta; and with Redondo (the greatest defensive midfielder of all-time at the time) getting an injury that just about ended his career when he arrived in Milan. Maybe we thought anyone we put as a defensive midfielder would discover some kind of magic mushroom in Valdebebas and become the next best player in the world at that position — even if it was David Beckham, Guti, Pablo Garcia, Emerson, or Gravesen.
Cambiasso would’ve solved a lot of problems — and we didn’t have to unearth him from anywhere. He was already in the squad and was really promising. People think he blossomed out of nowhere at Inter — but he was touted as a heir to Nando at a young age, came through Real Madrid’s ranks, was tactically astute, and was smooth on the ball. In a season where Real Madrid played a ton of Beckham - Guti as double pivot; Cambiasso was riding the bench for the most part before getting sold in the summer of 2004. He was the best defensive midfielder in the team at the time, and the best one Real Madrid would’ve had until Xabi Alonso came along.
More random memories from Kiyan’s vault of nostalgia, circa 1999 - 2009.
Rapid fire, let’s go.
The Raul shush: October 13, 1999
A common memory for anyone. The background to that goal, as I’ve written about before:
One of the most iconic moments Raul ever gave us was putting his fingers to his lips in the face of a raucous Camp Nou. That was 1999. It was one of the most heated and hostile Clasico matches in recent memory. We really never saw that kind of rage and bitterness until the Mou vs Pep beef rekindled years of lost time where the Clasico just kind of was. It was always good, always big, and always tense; but heated, violent, filled with hate and rage? We took a good decade-long hiatus from that post-Hierro/Rivaldo/Lucho/Redondo/Figo era.
That match in October of 1999 had everything. Between Raul’s opening goal — where he headed the ball past Ruud Hesp, taking advantage of some terrible near-post defending from Michael Reiziger — and his second goal in the 89th minute where he drew level, we saw Rivaldo hit the roof of the net with a left footed lazer, Morientes watch his back-heel-flick go just wide, Morientes have a goal wrongly disallowed for a phantom call where Abelardo tripped over his own legs, Reiziger put his cleat on Savio’s shin, Sergi clear a goal off the line with his hand (unpunished), Figo dribbling past Geremi and cutting in to score at the near-post with his left foot, Kluivert throwing an embarrassing tantrum at the referee and getting sent off as the powerless Guardiola tried to calm him down, Redondo palm Rivaldo’s face while the Brazilian milked every second of it, Savio get into a shoving match with Luis Enrique and Puyol, Luis Figo unapologetically chopping Salgado nowhere close to the ball, and a bunch of other scuffles — not to mention a back-and-forth attacking melee of goalscoring chances.
And somehow, all of that madness got lost (as it should) because Raul encapsulated exactly what kind of player he was in one moment. No matter the situation, Peak-Raul always found a way to put the team on his back. And by every measure, the team needed him more than ever in that emblematic moment. Consider this -- that was a terrible domestic season for Real Madrid (though, they were very successful on a European level). It was a season of great individual legends carrying the team in key moments — and this was one of them.
Roberto Carlos and Steve Mcmanaman were not in the team that night, and Del Bosque had to get really funky with the scheme — pushing Savio as some kind of wonky, advanced left-back, sliding in Ivan Campo as a sweeper (this is something Del Bosque generally liked to do in big matches regardless), and fielding three forwards (Raul, Anelka, Morientes) in front of Redondo and Geremi. Raul was the only player versatile enough who could bind the team and play as the creator in-behind the forwards while the more defensive-minded players behind him did the dirty work.
Things generally weren’t going Real Madrid’s way in that 2-2 draw. Figo was possessed that night, dribbling past (at will) any player who found themselves defending the flank, and even though Real Madrid played well (despite not scoring, Anelka’s dribbling and off-ball movement was really good, and he hit the bar too; while Geremi’s pace caused Barcelona problems all night and Redondo was tremendous in winning possession), they had big calls go against them. But when Kluivert was sent off, the team found momentum, and with the help of Clarence Seedorf who entered the match and injected some creativity and help in the midfield, clicked into another gear which Raul eventually capped late.
Intelligence, composure, cold blood, finishing — all traits of Raul we saw in that moment. Seven seconds before he scored the equalizer, just when Redondo had dispossessed Zenden, Raul was already moving into position — roaming in-behind Barcelona’s defense without the ball — and when Savio slipped Raul through, he was already in Abelardo’s blind spot. Raul latched on, clipped it over Hesp, and salvaged a point for Real Madrid in a very difficult game.
Those moments are peppered throughout Raul’s career. Real Madrid has a rich history of legendary players, but each generation has a defining player that has so many cojones pumped into his veins that you wonder just where in the universe they came from. These players, a handful of them, transcend everyone, and sit at their own table. Raul is one of the immortals, even if the peak of his powers was a shorter window than we had hoped.
Empty Olimpico: December 8, 2004
My first experience watching a match without spectators wasn’t against Legia Warsaw in 2016; but against Roma at the Olimpico in 2004 where UEFA had punished the home team for some fan violence in a match prior. It was just unthinkably weird to watch a game without fan noise for the first time, and took away from Ronaldo’s and Figo’s brilliant goals:
Guti, and Raul take over Olimpico: September 17, 2003
Those two were absurd that night, combining for three goals and three assists:
Speaking of the Olimpico, this Figo show:
The gulf in class: April 8, 2003
It wasn’t the scoreline — 3-1 — that stood out about Real Madrid’s quarter-final demolition against Manchester United in the Champions League quarter-finals; it was the football that Del Bosque’s men played that night. It was, the most beautiful football I can remember during that entire decade from Real Madrid. The next day, the English papers were writing about Manchester United facing a great team — that the English side were completely outclassed as they witnessed a lesson.
Among OG Ronaldo’s ability to bounce off defenders, Raul scoring two great goals to add to his Champions League tally, Luis Figo bullying Wes Brown, and Roberto Carlos constantly providing dangerous overloads, it was Zidane’s performance that stood out for me:
The Camp Nou Grinch: December 23, 2007
Pepe’s masterclass at the Camp Nou against Eto’o and Dinho’. One of the most underrated individual performances by a Real Madrid defender since the turn of the century:
Iker saves La Novena: May 15, 2002
Zidane’s thunderbolt rightfully took stage in Glasgow. But we must immortalize the way Iker came off the bench late for the injured Cesar, and churned in really important saves to prevent Leverkusen from equalizing:
Egg on Kahn: February 24, 2004
There is nothing like the notorious trash-talker, Oliver Kahn, making a big blunder and letting his team down. In this instance, in form of a Roberto Carlos free-kick:
“After something like that you want to escape, get out of the place as fast as you can,” Kahn said after the match. “Anyone who knows me realises that I will rise above it in the return leg. I will make it my responsibility to win the match in Madrid on my own.”
Of course, we all know Real Madrid advanced anyway.
The fetal position: March 10, 2009
An entire second half where I laid down in the fetal position, watching one of the most gutless and soulless Real Madrid performances I have ever witnessed:
Raul’s second: April 19, 2000
From the same game Redondo did this; I’m going with the hipster choice. Raul’s first touch and finish, just before Redondo’s timeless moment, was gorgeous:
All we heard before that entire match from the English press was that ‘Real Madrid weren’t on United’s level, blah blah blah’. I have no idea what they said after Raul, Redondo, Carlos, and McManaman humbled them — I was too busy celebrating.
Portillo heroics: February 25, 2003
Funny thing about that entire aforementioned story about Figo’s penalty miss in Turin, and how Real Madrid of ‘02-’03 were the best of the lot. They were so close to being eliminated in the second group-stage of the Champions League. Seconds away, in fact. Javier Portillo came off the bench to rescue the essential point in the 90th minute:
Portillo is an eternal enigma. He shattered Raul’s records for the youth teams, scored from 40 yards against Panathinaikos in his Champions League debut, and then scored a few other nice goals — all to disappear not long after.
Just imagine the butterfly effect if Portillo didn’t score that goal. We wouldn’t have seen either of the historic matches against Manchester United in the ensuing round.
Rui Costa dagger: November 26, 2002
Like I said, I have plenty of jarring memories floating around. It’s not all good.
AC Milan were an absolute giant in the early part of the millennium. That Real Madrid and Milan were drawn together in the same group that year was pure hype, and many expected them to face each other again in the final for a historic event. We lost that game in San Siro 1 - 0 while witnessing some great one-touch passing from Raul, Roberto Carlos, and Zidane throughout. But I’ll never forget how beautiful this Rui Costa through-ball was:
Slight consolation: Real Madrid won the return fixture at the Bernabeu, 3 - 1 — admittedly when Milan had already qualified from the group. In the process, we got to whistle Rivaldo, and give a standing ovation to Fernando Redondo in his return.
That match also boasted some exquisite touches from Zidane, devastating overloads from Roberto Carlos, and a Raul golazo. (In case you haven’t caught on, those three things were a staple of Real Madrid’s identity from 2000 - 2003.
Which leads me to an entire section on more memorable Raul moments in the Champions League (hipster choices only):
More memorable Raul moments in the Champions League (hipster choices only): 2000 - 2003
Not including the obvious Champions League final goals; but admittedly including one of my favourite goals against Barcelona, in the Champions League semi-final, and an assist to Zidane in that same tie.
We have to start with a goal that embodies everything from that era. Figo’s passing, Zidane’s touches, Roberto Carlos’s runs and connection with Zizou, and Raul’s finishing:
This Solari goal against Lazio: February 21 2001
The corpse of Nicolas Anelka rises: May 2000
As I wrote for Marca back in 2017:
Just two months after Real Madrid were dealt a blow by Bayern Munich in the group stages in 2000, Los Blancos went into the semi-finals of the Champions League as severe underdogs.
Not least because they were perceived as ‘riding their luck,’ after eliminating Manchester United in the quarter-finals, and because no team had ever beaten the two previous finalists - United and Bayern Munich - from the year before. Besides, this was a Bayern side that was on a mission.
They had been defeated in soul-gutting fashion at the Camp Nou in 1999, they were hungry and they had already feasted on Real Madrid that same season. Everything pointed to them finishing their deed once the two legs had passed.
On the other hand, Real were treading water in LaLiga, barely getting into the top five in a largely disappointing domestic campaign.
Then came Nicolas Anelka. He had been signed the summer before for just over 22 million euros from Arsenal, and was supposed to act as Raul’s strike partner moving forward.
He wasn’t. He didn’t score a single goal in his first five months at the club, and was largely outplayed by Fernando Morientes. Sporadically, Anelka would show signs of life but never truly showed the form from his Arsenal days.
Against Bayern, however, the Frenchman bamboozled both Jens Jeremies and Thomas Linke to finish into the roof of the net, past Oliver Kahn.
He also scored in the second leg:
Guti, the striker: 2000 - 2001
Under-discussed: An entire season where Guti played as a striker because of injuries that Fernando Morientes suffered. Guti scored 18 goals that season. My HAZ:
The Zidane show: January 5 2003
RIP anyone wearing orange that night:
Tamudazo: June 9, 2007
The one Capello season (stint 2.0) was the best among the ‘dark years’ post-2003. It was a season defined by remontadas and Pichichi Van Gol heroics. Real Madrid went into the penultimate (and ultimate) matchday(s) level on points with Barcelona, but slightly ahead on the head-to-head rule. They were losing away to Zaragoza; while Barcelona were ahead against Espanyol. In virtually the exact same moment (the games were being played simultaneously), in the 90th minute, Van Nistlerooy equalized for Real; while Tamudo equalized for Espanyol. An immortal moment referred to as ‘minuto magico’:
The underrated hilarity of Ronaldo’s immortal hat-trick: April 23, 2002
It’s not that Ronaldo’s hat-trick was hilarious. It was epic. It’s that the defending from both teams was just so comically terrible:
Roberto Carlos free-kick from 500 yards against Barcelona: February 26, 2000
A fun match, so we might as well include the full clip. Included: Redondo and Hierro not backing down from the shameless Rivaldo, and Morientes rounding out a nice 3-0 victory in a Clasico that happened pre-Figo-switch:
Iker Casillas’s wrath: Perpetual
Anytime Real Madrid conceded a chance or a goal, regardless of how it happened:
Iker Casillas crying: Every time Real Madrid won a trophy
When the greatest goalkeeper of all time who loves this club cries, you do too — that’s the rule.
The great away jersey of 1999 - 2000
Double-golazo: January 5, 2002
Real Madrid vs Super Depor ‘back in the day’ was always hyped, and never easy (as Real Madrid found out losing the Copa final at home to them during the centenary). In 2002, we witnessed two incredible goals: 1) Zidane’s famous dribbling sequence and left-footed shot; and 2) Raul’s control and right footed shot. Of the two, Zidane’s is better remembered; but maybe that’s because it was so good that Raul’s looked worse in comparison. But both goals were great.
Jose Antonio Reyes shakes the Bernabeu to win the title: June 17, 2007
David Beckham’s last match for Real Madrid:
A nightmare: November 9 2003
Everything that was wrong with Real Madrid’s decline was manifest that night at the Sanchez Pizjuan, where Real Madrid lost 4-1 against Sevilla. Post-peak legends (Figo, Raul, and Zidane) ‘supported’ by a double-pivot of Beckham and Guti and a back-four of Pavon, Ruben, Raul Bravo, and Helguera.
Dani Alves and Reyes were great that night.
Figo’s inevitable goal vs Barcelona: November 4, 2001
It was coming, and it was anticipated.
Figo’s goal against Barcelona didn’t come in the Camp Nou (which would’ve been sweeter), but he did get it in a 2-0 win over Barcelona in 2001 at the Bernabeu. Some really nice play between Zidane, Makelele, and Raul (who dummied the pass) to Figo:
Placido Domingo bringing the goosebumps with Himno Centenario
Saying goodbye to Zizou: May 7 2006
Pasillo: May 7 2008
“They were better than us in everything,”
- Víctor Valdés
I have more, I promise.