5 biggest round-of-16 upsets in UEFA Champions League history

Real Madrid v Club Atletico de Madrid - UEFA Champions League Final
Will we see one this knockout stage?

#4 Lyon v Real Madrid (2009-10)

Lyon v Real Madrid - UEFA Champions League
Lyon v Real Madrid - UEFA Champions League

Real Madrid have not always been the all-conquering force in Europe, despite their record 11 titles. For a spell in the early part of the millennium, they suffered a remarkable jinx as they were unable to get past the quarter-final phase.

Manuel Pellegrini’s side had impressed in the group phase, steamrollering their way to the top of the standings with a succession of strong victories, seeing off Milan, Marseille and Zurich in the process. In La Liga, meanwhile, they were looking good, even in comparison to a formidable Barcelona team, and even a shock upset against Alcorcon in the Copa del Rey did not suggest they would find an ailing Lyon side too much of a hurdle.

At Stade Gerland, however, a goal from Jean II Makoun shortly after the interval gave the French side an advantage to carry to Spain three weeks later.

The world seemed to have been put to rights when Cristiano Ronaldo struck after six minutes for the hosts, yet 15 minutes from time Miralem Pjanic, a product of the OL youth system, carried the French side to perhaps their most famous ever success.

It was to prove a season of frustration for Los Blancos, who won 18 of their last 20 matches in La Liga but still finished second to Barca, despite picking up 96 points.

Lyon, meanwhile, saw off Bordeaux in the quarter-finals but came unstuck against Bayern Munich in the quarter-finals.

Quick Links