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#3 Alfredo di Stefano (November 1990 - March 1991; 42.86% win rate)
Alfredo di Stefano was Real Madrid's all-time top goalscorer until a certain Cristiano Ronaldo emerged to break most of his scoring records. Di Stefano scored a whopping 487 goals in 669 career appearances in his club career. Over 300 of those goals came for Madrid, making him their highest goalscorer at that time.
One would scratch their head seeing Di Stefano on this list, considering his staggering exploits as a player. However, he didn't enjoy the same success from beyond the touchline. His second managerial stint at the club was something to forget.
In his first stint, Los Blancos won 63, drew 23 and lost 22 of his 108 games in charge, scoring 192 goals and conceding 113. Fast forward a few years, and Real Madrid struggled under the legend once again.
Madrid's win percentage dropped from 59% in his Di Stefano's first spell to 42%. In 21 games, Di Stefano managed nine wins, three draws and nine losses. That made him one of the only managers in Real Madrid's history to have the same number of wins and losses after 20 games in charge of the club in multiple stints.
It seemed as though each time Alfredo di Stefano returned to the Bernabeu, his reputation got diminished.
#2 Julen Lopetegui (June 2018 - October 2018; 42.86% win rate)
Julen Lopetegui came to Real Madrid at a time when arguably any manager in world football would have been intimidated.
Los Blancos were on the back of three successive triumphs in the UEFA Champions League. They had initiated a shift of power from FC Barcelona's hands into their own. Zinedine Zidane was the flag-bearer for the side, managing them back to the top. His successor, though, failed to reach those lofty heights.
Lopetegui was a goalkeeper during his playing days, making 317 appearances, with most of them for Rayo Vallecano. Soon after retiring as a player in 2002, he joined the managerial ranks in Spain's youth set-up as a coach for the U-17s. His first major club position was as manager of FC Porto between 2014 and 2016. After that, he managed Spain before he was appointed the Real Madrid boss.
In his 14 games in charge, Madrid won six, drew two and lost six games, scoring 21 and conceding 20 goals. What exacerbated matters was that his first game in charge was a 4-2 loss to bitter rivals Atletico Madrid in the UEFA Super Cup in 2018. He also endured a 5-1 reverse at Barcelona in the league in October 2018.
Big defeats against their fiercest rivals are inexcusable at a club like Real Madrid, and Lopetegui learnt that the hard way.
#1 Amancio Amaro (May 1984 - April 1985; 40.43% win rate)
Amancio Amaro Varela, commonly known simply as 'Amancio' is a former Real Madrid, Deportivo La Coruna and Spain player. He played as a wide right or right winger. The Spaniard scored 173 goals in 436 appearances in club football, and 11 in 42 appearances for his national team.
Amancio is another former player-turned-manager on this list, and unfortunately, his record is the worst. In his 47 games in charge, Real Madrid won 19, drew 13 and lost 15, scoring 69 goals and conceding a whopping 52. That gave him a win rate of just 40% - extraordinarily poor by Real Madrid's standards. As you can tell from these numbers, the club was being pulled in two directions.
While they got some wins, the way they dropped points in draws and defeats was absymal. Los Blancos conceded more than one goal per game throughout Amancio's tenure. That's one of the biggest red flags for a side looking to win championships.
It is unfortunate to see players with glorious careers not enjoy the same success in their managerial stints. That's because managing a team is a different ball game than playing for one, making the transition challenging.
