In what is now considered a modern European classic, Manchester City and Real Madrid meet for the fourth consecutive year. This unexpected showdown between the last two Champions League winners takes place in the Playoff round for a spot in the Round of 16, as both teams arrive in a precarious moment in this debut season of the tournament’s new format.

A disappointing group-stage campaign, with losses to Lille, AC Milan, and Liverpool, has led the reigning champions to the worst possible draw. Real Madrid now faces its most feared opponent—Manchester City—a team it has never beaten at the Etihad Stadium. Their past encounters have produced unforgettable moments, including epic battles that paved the way for Madrid’s last two Champions League triumphs.

Recent history recalls City’s dominance, as Pep Guardiola’s side has eliminated Real Madrid in two of their last three meetings in the competition. However, while Madrid survived last season’s Etihad battle to advance on penalties en route to its 15th European title, there is no feeling of inferiority this time around. Carlo Ancelotti’s team leads LaLiga, while City, now 15 points behind the Premier League leaders, is all but out of the title race.

Ancelotti’s challenge is to guide his team to victory in a high-stakes clash. Aside from a comfortable win over Borussia Dortmund in the Super Cup, Madrid has struggled against top opposition this season. Heavy defeats in both Clásicos, an uninspired showing at Anfield against Liverpool, and losses to Athletic Club at San Mamés highlight their inconsistency. Meanwhile, their Madrid derbies against Atlético have both ended in draws.