Tonight, for the second time in under a month, Real Madrid face a Champions League matchup with a Benfica team managed by Los Blancos’ former head coach, José Mourinho. The knockout-round playoff tie comes 20 days after As Ágiuas humbled Madrid in Lisbon, in a win that earned the Portuguese club an unlikely spot among the qualifiers from the league phase.
Capped by keeper Anatoliy Trubin’s last-gasp goal, Benfica beat Madrid’s nine men 4-2 at the Estádio da Luz on Jan. 28 - with Trubin’s dramatic late header sending the two-time European champions into the knockouts on goal difference. The Ukrainian became the first ever goalkeeper to score against Madrid in European competition; an ignominious milestone for the visitors, rounding off a night on which they were fortunate not to concede more than four.
Mou’s maiden Madrid win
Trubin heroics aside, Benfica’s matchday eight win was also notable as Mourinho’s first ever victory against Madrid in his nearly three-decade career as a head coach. In all, the 63-year-old has now come up against the LaLiga giants six times, with three different clubs - and has mostly endured defeat.
Early in his two-and-a-half-season, breakout spell as FC Porto boss, Mourinho and the Dragoes were pitted against Real Madrid four times in two years. In 2001/02, the teams were drawn together in the second group phase of the Champions League, facing off home and away in February 2002. Porto, who had appointed Mourinho just a month earlier, lost by a single goal both at the Bernabéu and in Oporto, on their way to finishing bottom of Group C. Madrid, meanwhile, topped the group unbeaten - and went on to lift their ninth European title that May.
In 2002/03, Mourinho’s Porto were again paired with Real Madrid at the Champions League’s round-robin stage - this time in the opening group phase. Again, Madrid were undefeated on their way to finishing first, their results including a 3-1 victory in Portugal. However, Porto earned a point in the Spanish capital, Derlei’s 35th-minute penalty cancelling out Santiago Solari’s early opener. And, thanks chiefly to home-and-away wins over Marseille, Porto qualified behind Madrid.
Where it had been Madrid who had proceeded to lift the trophy in 2001/02, this time it was Porto who rolled through the knockout rounds, before securing an unexpected second continental crown with a 3-0 final victory over Monaco.
Partly because, between 2010 and 2013, Mourinho was himself the Real Madrid head coach, the Portuguese did not face Los Blancos for another 13 years after Porto’s Champions League-winning season. In August 2017, during his two-and-a-half year stint in charge at Manchester United, he led the Red Devils into a UEFA Super Cup clash with Madrid, who had just clinched the second of three straight European titles under Zinedine Zidane.
United, who had won the Europa League under Mourinho the previous season, were beaten 2-1 in Skopje, as the Champions League holders triumphed through first-half goals by Isco and future Old Trafford player Casemiro. Romelu Lukaku replied for United in the second half.