Real Madrid Sheriff GFXGetty/Goal

The biggest upset in Champions League history: How did Real Madrid lose to Sheriff?!

Match statistics: Real Madrid 1-2 Sheriff

Back under the lights at the Santiago Bernabeu, the stage was set for the kings of Europe, record 13-time winners Real Madrid, to rack up a big win on their homecoming.

Instead they skulked into the night with bloody noses, wondering what hit them.

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It was two bullets from Sheriff Tiraspol, minnows from Moldova, formed in 1997 and eliminated from Europe last season by Dundalk.

It was their first ever Champions League away victory, and there can be no better place to have pulled it off.

Carlo Ancelotti shuffled his pack, confident that even some of his reserves would be able to sweep past the visitors without fuss. Especially when the reserves are players like Eden Hazard and Fede Valverde.

However, Madrid failed time and time again in front of goal, and it took a penalty from Karim Benzema to level Jasurbek Yakhshiboev's first-half header.

Los Blancos pushed for a winner, but Sebastien Thill struck in the 89th minute to produce possibly the biggest ever upset in Champions League history, given the disparity between the teams.

On sheer chances, Madrid dominated, but football does not work like that. It would be boring if it did.

“We had control of the game, their keeper made a lot of saves,” insisted Casemiro afterwards. “We have to congratulate them. They scored two goals.”

Madrid might have scored far more, but Benzema curled wide of the far post and Vinicius Junior returned to his profligate self from last season.

At least the Brazil international's footwork was still tip-top, going down twice in the box with the second of those leading to the penalty, dispatched by Benzema coolly.

At that point, it looked a formality that Madrid would go on to win the game. Ancelotti threw on Luka Modric, Luka Jovic, Rodrygo and Toni Kroos, the latter making his first appearance after injury.

The Bernabeu roared, with fans back in the stadium to watch the team in the competition they cherish the most for the first time in 580 days.

Modric was denied by goalkeeper Georgios Athanasiadis’s face. It will smart in the morning, but it was perhaps the best of his 10 saves, and that pain will be a reminder of his and Sheriff’s marvellous night.

Sheriff celebrate 2021-22Getty Images

Meanwhile Ancelotti put the ‘real mad’ in Real Madrid on the touchline, uncharacteristically rowing with officials before being issued a yellow card.

One of Madrid’s best chances fell to substitute Jovic, but the Serbia striker fluffed his lines in front of goal instead of giving his faltering career a much needed shot in the arm.

Instead it was Thill, a man with a tattoo of himself dreaming of the Champions League on his leg, who became the matchwinner. And the goal was something out of his wildest fantasies, a rip-roaring strike from the edge of the box which seared past Thibaut Courtois and into the top corner. 

For Madrid, it was a nightmare.

Of course, the win at Inter in their opening game means they are still well placed in the group. Last season, they started with a defeat by Shakhtar Donetsk and still progressed. Nobody in the capital believes this is a significant setback to their hopes.

But it does bruise their ego, with president Florentino Perez undoubtedly stinging after this humiliating capitulation.

It is a night Sheriff will never forget, and no Madrid supporters will be able to either.