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4. Lyon 2-1 Real Madrid: 2009-10
Miralem Pjanic's strike eliminated Real Madrid in 2009-10
Real Madrid had a torrid time in European competitions after their famous 2002 title triumph. A round of 16 elimination at the hands of Juventus in 2004-05 would start a trend of Los Blancos failing to get past the same stage for the next six years despite possessing stars like Luis Figo, Zinedine Zidane, Michael Owen and David Beckham.
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By the 2009-10 season, Real had done away with the old guard while ushering in a new 'Galacticos' era with the likes Cristiano Ronaldo, Kaka, Gonzalo Higuain and Karim Benzema and were determined to break the jinx. That year saw Real drawn against French side Olympique Lyonnais at the round of 16 stage of the Champions League. The French side had just been displaced as Ligue 1 monarchs by Bordeaux after six straight titles and were a side in transition.
That did not stop Lyon from winning the first leg 1-0 at the Stade Gerland courtesy of a Jean Makoun wonder strike. Ronaldo and co. were desperate to overcome the deficit in the second leg at the Santiago Bernabeu and CR7 cancelled it out within the first six minutes.
Despite being on the backfoot for much of the opening half, Lyon had a few chances at Madrid's goal and Maxime Gonalons, Lisandro and Sidney Govou tested Casillas. Lyon were becoming increasingly confident and regained the lead in the tie with 15 minutes left.
Kim Kallstrom and Cesar Delgado sliced open the Madrid midfield and fed the Argentine Lisandro, who executed a first time lay-off that saw the ball reach Miralem Pjanic. The Bosnian beat Casillas at his near post and Real were left needing to score two more to progress.
Los Blancos could muster none and Lyon went through to the quarterfinals where they had the pleasure of eliminating domestic rivals Bordeaux to reach a first Champions League semi-final.
As for Real, that round of 16 jinx would be broken the very next year when they beat none other than Lyon 4-1 on aggregate.
