Mourinho Has Not Won a Champions League Knockout Match for 12 Years: Can His Return to Real Madrid End the Drought?

It has been 12 years since Mourinho last won a Champions League knockout match. On Tuesday night, his first Champions League match as Real Madrid manager will coincidentally see his former club Inter Milan visit the Bernabeu.

12-year knockout-stage drought

After the end of the 2009-10 season, Mourinho had just led Inter Milan to a Champions League treble before taking charge of Real Madrid. At the time, many believed he was the most likely person to help Real Madrid end their long wait for a 10th Champions League title. However, in the following three seasons, the Real Madrid side featuring Cristiano Ronaldo, Benzema and Kaka was eliminated in the semi-finals each time.

After leaving Real Madrid in 2013, Mourinho took five clubs through eight Champions League campaigns, including qualifying rounds. However, his last victory in a Champions League knockout tie came in the 2013-14 season. That year, his Chelsea reached the semi-finals before being eliminated by Atletico Madrid, with Thibaut Courtois, then on loan from Chelsea to Atletico, playing a key role.

Repeated failures to advance

In the 2014-15 season, Mourinho's Chelsea featured Courtois, Hazard, Fabregas and Diego Costa. In the last-16 tie against Paris Saint-Germain, Ibrahimovic was sent off early in the second leg in London, giving Chelsea a numerical advantage, but Paris still controlled possession and advanced on away goals. Gary Neville said on Sky Sports at the time: "It is embarrassing. They thought they would easily reach the quarter-finals, but they were knocked out."

In the following season, Chelsea topped their Champions League group, but Mourinho was dismissed in mid-December due to poor Premier League results. In the 2017-18 season, he led Manchester United back to the Champions League, winning five of six group matches to advance comfortably. In the last 16 against Sevilla, United drew 0-0 away in Spain in the first leg, with De Gea making several saves and being named the best player of the match. Back at Old Trafford in the second leg, the game remained goalless for a long period, with fans chanting "attack, attack, attack." In the closing stages, Sevilla's Ben Yedder scored twice, and Lukaku's goal was not enough to change the result. After the match, Mourinho refused to take responsibility for the defeat and instead spent 12 minutes explaining that Manchester United lacked things at the "football" level.

Real Madrid have won the Champions League six times since then

Since Mourinho left Real Madrid in 2013, the club has won the Champions League six times: Ancelotti led the team to three titles in 2014, 2022 and 2024, while Zidane guided them to three titles in 2016, 2017 and 2018. Now Mourinho has returned to Real Madrid, and his first Champions League match is against Inter Milan, the club he once conquered Europe with. Whether he can end his personal 12-year winless run in Champions League knockout matches is the biggest talking point on Tuesday night.