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#7 Antonio Conte | €944 million
The Italian masterminded Inter Milan's rise to the pinnacle of Italian football, ending Juventus' nine-season long Scudetto winning streak.
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Antonio Conte was also responsible for kickstarting Juventus' dominance of Italian football, guiding the club to three consecutive Scudettos between 2011 and 2014. The 52-year-old also won a domestic double with the Bianconeri in the 2012-13 and 2013-14 seasons. After a trophy-laden spell in Italy, Conte took over as the coach of the Italian national team for a two-year period.
Conte's next club assignment was in the Premier League with Chelsea. During his two-season stay at the club, Conte led the Blues to Premier League and FA Cup glory. He returned to his homeland in 2019 to take over as Inter Milan boss.
The Italian guided the Nerazzurri to their first Serie A title in 11 years. Conte signed 84 players in the 21st century, spending a total of €944 million.
#6 Diego Simeone | €985 million
The Atletico Madrid manager will go down in the history books as one of the best managers of the 21st century, having been responsible for ending Barcelona and Real Madrid's La Liga dominance.
Spain's big two have won a combined total of 60 La Liga titles. Only seven other clubs have won the La Liga title, and Atletico Madrid have achieved the feat twice during Simeone's tenure. Barcelona assembled one of the greatest teams in footballing history in the late 2000s/early 2010s, while Real Madrid became the only team to win three successive UEFA Champions League titles in the mid-2010s.
However, none of these world-class outfits could deny a well-drilled and well-oiled Atletico Madrid outfit under Diego Simeone. The Argentine has won two La Liga titles, two UEFA Europa League titles, two UEFA Super Cups, and one Copa del Rey and Supercopa de Espana apiece.
The Argentine has spent a total of €985 million on 68 players across seven different clubs.
#5 Massimiliano Allegri | €1.06 billion
The first manager to enter the billion-euro spending club is current Juventus boss Massimiliano Allegri, who has signed 96 players since the dawn of the century.
The Italian has managed eight different clubs since the 2000s in his 18-year managerial career. Allegri took over the reins of Juventus from Antonio Conte in 2014 and further enhanced the club's reputation in Italian and European football. During his five-year stay at the club, Allegri won five consecutive Scudettos, five domestic doubles and one domestic treble in the 2015-16 season.
The Italian also won the Serie A title as manager of AC Milan in the 2010-11 campaign and the Supercoppa Italiana in 2011-12. Allegri has spent a whopping total of €1.06 billion in his managerial career so far.
#4 Manuel Pellegrini | €1.16 billion
The Argentine has spent an eye-watering €1.16 billion on player recruitment in the 21st century, mainly during his three-year stay at the Etihad.
Manchester City signed Fernandinho for €40 million and Alvaro Negredo for €25 million during Pellegrini's first season in charge. The Cityzens splurged some serious cash during the Argentine's last season at the helm. City signed Kevin de Bruyne for €76 million, followed by Raheem Sterling for €63.7 million and Nicolas Otamendi for €44.5 million.
Pellegrini is currently one of the most experienced managers in world football, with a managerial career dating back to 1988. He has managed 10 different clubs since the turn of the century, spending a total of €1.16 billion on 88 different players.
