Mourinho's 37-Game Unbeaten Run Ended by the Only Team That's Never Let Real Madrid Off Easy

José Mourinho's long unbeaten run as a manager came to an end on Friday night. The team that ended it has a habit of doing exactly this to Real Madrid.

Real Betis beat Real Madrid 1-0 at the Estadio de La Cartuja. The result stopped Mourinho's personal run of 37 matches without losing, a streak built across three different clubs: Benfica, Fenerbahçe, and now Real Madrid.

He was three unbeaten games away from matching his own record of 40, set at Chelsea, and four away from breaking it. Betis stopped him at 37.

It also ended Real Madrid's perfect start to the new season.

What makes this loss sting more than a normal early-season upset is who caused it, and how.

This is not the first time Real Betis have beaten Real Madrid in a way that mattered far beyond three points. And there's a personal twist too, the man who scored the winning goal is someone Mourinho once managed, before their relationship deteriorated.

Here's the full story, from Friday night's match, back through the history behind it.

What happened on Friday night

Real Madrid had the better of the game for long spells. Vinícius Júnior hit the post in the first half. Later on, Kylian Mbappé struck the crossbar. Chances kept coming, but the ball wouldn't go in.

Betis stayed patient and waited for their moment. With ten minutes left, substitute Troy Parrott was quickest to react after goalkeeper Thibaut Courtois parried a header away.

Courtois saved the header, but couldn't hold on to the ball. It fell right in front of Parrott, and he shot it into the net from close range to put Betis 1-0 up.

It was his first appearance at home for the club, and he'd only been on the pitch for around 13 minutes.

Real Madrid had ten minutes left to find an equaliser, and almost did. Substitute Carlos Espí scored what looked like a stoppage-time leveller with a spectacular bicycle kick, but it was ruled out after a VAR review for offside.

Then, deep into added time, Real Madrid won a penalty of their own, after Natan fouled Vinícius in the box.

Kylian Mbappé stepped up to take it. Betis goalkeeper Álvaro Valles guessed the right way and saved it, sealing the win.

Mourinho didn't have an explanation afterward.

"Sometimes, and you don't know why, you lose and you can't explain it," he said. "We were very dominant, controlling absolutely everything. There was plenty of attacking play and plenty of chances to score."

"If it had ended in a draw, we'd have been frustrated because we did so much more. Imagine now that we have lost."

There was also a personal edge to Parrott's goal that had nothing to do with tactics.

Mourinho gave Parrott his first-team debut for Tottenham back in December 2019, when Parrott was just 17. He even gave the teenager the match ball afterward.

But the relationship didn't stay warm for long. Mourinho later criticised Parrott's attitude in public, and the young striker made only four senior appearances for Spurs before being sent out on loan, first to Millwall, then to Ipswich, where things didn't go much better.

Parrott eventually rebuilt his career in the Netherlands with AZ Alkmaar, before Betis signed him this summer for around £17m.

On Friday, the teenager Mourinho once criticised scored the goal that handed him his first defeat since returning to Real Madrid.

The matches that feel just like this one

This isn't the first time Real Betis have beaten Real Madrid in a moment that mattered for more than just the three points.

Go back to September 2017. Real Madrid had just won the league and the Champions League the season before.

They'd also scored in 74 consecutive matches. That night, Cristiano Ronaldo was returning from a five-match ban.

Real Betis ended Madrid's scoring run and spoiled Ronaldo's return in the same match. Antonio Sanabria scored deep into stoppage time to win the game 1-0 at the Bernabéu. It was Real Madrid's first match in 74 games without scoring at all.

Then there's last season. In April 2026, Real Madrid travelled to La Cartuja in the middle of a title race with Barcelona, needing a win to keep their hopes alive.

Vinícius Júnior put them ahead in the 17th minute, his 125th goal for the club.

It wasn't enough. Héctor Bellerín, a former Barcelona player now at Betis, equalised in the fourth minute of stoppage time. Real Madrid were held to a draw, and Barcelona went on to win the league that season.

That's three matches now, across three completely different Real Madrid squads and three different managers. And every single one of them came down to drama right at the very end.

Mourinho arrived at Real Madrid this year with plenty to take on, a talented squad, huge expectations, and a midfield rebuild that shaped much of his summer.

What he may not have fully realised is that he also inherited a fixture with a history of going wrong at the worst possible moment. On Friday night, it happened to him too.