In the 21st century, Real Madrid have managed to win the Copa del Rey twice, but there are far more bad memories than good ones.
Since the turn of the century, Los Blancos have been eliminated by third-tier sides no fewer than five times – an inexcusable record for a team the size of Real.
Let’s take a look at which of those defeats hurt the most.
For Real, the 2014/15 Copa del Rey was nothing short of a shambles.
Drawn against lowly Cadiz in the fourth round, Real roared to a 3-1 win in the first leg and looked as dominant as you’d expect, but the tie didn’t even make it to a second leg.
Real were actually expelled from the competition after they started winger Denis Cheryshev, who was actually suspended from the game after picking up too many yellow cards in the 2013/14 tournament.
There was no embarrassing defeat for Rafa Benitez’s men. Instead, they were just really, really stupid.
When he took over from Fabio Capello, Bernd Schuster promised to bring attacking football back to the Santiago Bernabeu, but that came at the expense of good defending against Real Union in 2008.
A second string Real side fell 3-2 to the minnows in the first leg, but Schuster declined to make too many changes for the next leg. He brought in star striker Raul but left a lot of his main guys at home, and he paid for it.
Real were better in attack but could not keep Union out. They were 4-2 up in the 89th minute, when Eneko Romo popped up with a goal that saw the third-tier side win on aggregate.
It was naive of Schuster to be so ill-prepared for the second leg, but in his defence, a team which featured Fabio Cannavaro, Wesley Sneijder, Rafael van der Vaart and Marcelo should have been good enough.
Vicente del Bosque left a lot of his big names at home for the trip to Toledo in 2000, but they were still more than strong enough to get a result here.
Fernando Morientes started up front and the centre-back duo of Fernando Hierro and Manolo Sanchis joined at the back, but that didn’t stop Real from going two down within 14 minutes.
Savio pulled one back in the 19th, but Real were left banging away at a brick wall for the remainder of the game.
This was the first Copa del Rey under new president Florentino Perez, who had just kick-started the Galacticos era by signing Luis Figo and promising to make Real the best team in history. Awkward.
In a season in which Zinedine Zidane nearly lost his job as Real limped their way into the Champions League knockout stages, the boss found himself staring over the edge of the cliff again after falling to Alcoyano in the third round.
With the pressure already on in the aftermath of elimination from the Spanish Super Cup a few days earlier, Zidane put out a second-string side, with Casemiro the only regular starter in the team, but even Real’s academy side, who play at the same level as Alcoyano, would have been ashamed with the performance.
Real took the lead but were pegged back and taken to extra-time, and even though Alcoyano had a man sent off shortly after the restart, they still managed to score the winning goal.
In extra-time, Toni Kroos, Eden Hazard, Marco Asensio and Karim Benzema were all on the pitch, but Real looked lifeless. They were sloppy at both ends of the field and were left licking their wounds by a team who were playing in the fourth tier in 2019/20.
From start to finish, Real were utterly atrocious when they faced off against Alcorcon in 2009/10. It was a two-legged tie, and Manuel Pellegrini’s men still couldn’t manage to win.
Just describing them as losses doesn’t do it justice. Real were thumped 4-0 in the first leg, with the first three goals coming in the first half!
The defence was undoubtedly a reserve lineup – Christoph Metzelder and Raul Albiol shielded Jerzy Dudek in goal – but in attack, all three of Raul, Ruud van Nistelrooy and Karim Benzema failed to break Alcorcon down.
The second leg saw Pellegrini go for a front four of Raul, Van Nistelrooy, Kaka and Gonzalo Higuain (the team’s top scorer that season), but they only managed to pull one back in the 81st minute, and it was Rafael van der Vaart who scored it.
The whole thing became known as Alcorconazo in Spain as the press mercilessly ripped into Pellegrini for his shortcomings, and it’s still spoken about to this day.