Jurgen Klopp and Liverpool moved a huge step closer to the Champions League quarter-finals on Wednesday evening, securing a 2-0 win at Inter Milan to take control of their last 16 tie.
The win over the Italian champions was an impressive result for Klopp, one which saw the German reach a milestone as he celebrated his 50th win in the Champions League as a manager.
Klopp becomes just the eighth coach to have achieved the feat and following his achievement we look at each of the managers to have registered 50 victories amongst Europe’s elite.
Jurgen Klopp – 50
Liverpool’s win at the San Siro saw Klopp reach 50 wins in the Champions League, becoming the first ever German manager to have achieved the feat.
Klopp’s career in the competition has seen him reach three Champions League finals, losing his first two with Borussia Dortmund (2013) and Liverpool (2018) respectively before finally winning club football’s biggest prize with the latter during the 2018/19 season.
Jurgen Klopp has turned Liverpool into a European super power 😤
— ESPN FC (@ESPNFC) February 16, 2022
The 54-year-old has turned Liverpool into challengers both at home and in Europe since his arrival on Merseyside in 2015, with the Reds again among the favourites for success in this season’s competition.
The win over Inter Milan leaves Liverpool within reach of the quarter-finals as the Merseysiders look to reach a third final in just five seasons.
Rafael Benitez – 53
Rafael Benitez has 53 wins in the Champions League, with the Spaniard having managed a number of clubs in Europe’s leading competition including Valencia, Liverpool, Inter Milan, Real Madrid and Napoli.
Benitez’s best period in the Champions League came during his six-year spell at Liverpool, with his debut campaign seeing the Reds upset the odds to be crowned champions of Europe.
Happy 60th birthday to Rafael Benítez:
🏆 La Liga
🏆 UEFA Cup
🏆 Champions League
🏆 UEFA Super Cup
🏆 FIFA Club World Cup
🏆 Coppa Italia
🏆 FA Cup
🏆 UEFA Europa League
The third manager to win UEFA Cup & Champions League in successive seasons. pic.twitter.com/5c6yetldCn
— Squawka Football (@Squawka) April 16, 2020
Liverpool came from three goals down to beat AC Milan on penalties in an unforgettable final in Istanbul and over the following seasons became regulars in the latter stages.
Benitez also guided the club to a second final in 2007, though defeat in Athens saw AC Milan gain revenge for their dramatic loss two seasons earlier.
Louis van Gaal – 57
Louis van Gaal was manager of the cult Ajax side that won the Champions League in 1995, as the Dutch side’s talented team completed an entire Eredivisie and European season without defeat.
Ajax’s inexperienced side beat AC Milan in the final to be crowned the continent’s finest, before losing the following season’s final against Juventus.
Van Gaal’s side played fine football before Europe’s wealthiest clubs dismantled the core of the side, bringing an end to an unforgettable era for Ajax.
Van Gaal later had two spells at Barcelona and a two-year reign with Bayern Munich, guiding the latter to the 2010 Champions League final before suffering defeat to Jose Mourinho and Inter Milan.
Jose Mourinho – 81
Jose Mourinho announced himself to the world as the confident coach of a FC Porto, leading the Portuguese side to a stunning Champions League win during the 2003/04 campaign.
Mourinho was intoxicating during his initial emergence on the European scene, later taking charge of European giants in Chelsea, Inter Milan and Real Madrid.
— UEFA Champions League (@ChampionsLeague) May 26, 2021
Perhaps his greatest achievement – even exceeding Porto’s shock success – came when leading Inter Milan to a historic treble during the 2009/10 season, their Champions League run including the elimination of a formidable Barcelona side in the semi-finals.
Mourinho’s success and reputation has been on a gradual decline in the decade since, but he will be hoping to lead current side Roma back into the Champions League after taking charge at the Stadio Olimpico last summer.
Arsene Wenger – 86
Arsene Wenger holds the unwanted record of being the only manager on this list not to have won the Champions League, coming agonisingly close without succeeding during a 22-year reign at Arsenal.
Wenger enjoyed huge success during the early seasons of his spell in North London, winning three Premier League titles in just seven seasons across the turn of the millennium, including the Gunners’ famed unbeaten 2003/04 campaign.
European success proved elusive despite reaching the Champions League final in 2006, losing to Barcelona in Paris after seeing goalkeeper Jens Lehmann become the first person to be sent off in a European Cup final after just 18 minutes.
Arsenal reached the semi-final under Wenger three seasons later, but the club’s inability to turn domestic success into consistent continental challenges proved a disappointing aspect of his illustrious tenure.
Pep Guardiola – 91
Pep Guardiola is closing in on a century of wins in the Champions League, having racked up his 91st victory following Manchester City’s 5-0 thrashing of Sporting Lisbon on Tuesday evening.
Guardiola’s first season with Barcelona saw him lead the Catalan side to Champions League success, beating Manchester United 2-0 in the final in Rome.
Barcelona defeated the same opponents in the 2011 final, with Guardiola’s team often cited as the greatest club football has seen following a sustained period of spellbinding football.
👨🎓 A Barcelona masterclass #OTD in 2011! 📕
— UEFA Champions League (@ChampionsLeague) May 28, 2021
Having also reached three consecutive semi-finals during his time in charge of Bayern Munich, he guided Manchester City to the final in 2021 before defeat to Chelsea in Porto.
City are the favourites to go one better and win a first Champions League trophy this season, with Guardiola’s record of wins expected to increase in the coming seasons.
Carlo Ancelotti – 94
Carlo Ancelotti is one of just three managers to have won the European Cup/Champions League on three occasions, a feat matched by only Bob Paisley and Zinedine Zidane.
Ancelotti led a superb AC Milan side during the early 2000s, one which won the Champions League on two occasions under the Italian’s guidance, beating Juventus (2003) and Liverpool (2007).
Ancelotti could perhaps have enjoyed even greater success with the Rossoneri, but infamous collapses to Deportivo La Coruna in the 2003/04 quarter-finals and Liverpool in the 2005 final prevented a chance at four in a row.
After spells with Chelsea and PSG he led Real Madrid to the fabled ‘La Decima’ in 2014 and now, in his second spell with the Spaniards, will be looking to extend the club’s record as 13-time winners.
Alex Ferguson – 102
Sir Alex Ferguson was a two-time winner of the Champions League, during a career that saw the Manchester United icon become world football’s most successful ever manager.
Ferguson’s first triumph in Europe came after leading the Red Devils to the treble in 1998/99, an astonishing final few minutes seeing United score twice in stoppage time to turn defeat into victory against Bayern Munich.
🏆 He went on to win 38 trophies 🤯 pic.twitter.com/7ujKmvxy5y
— UEFA Champions League (@ChampionsLeague) November 6, 2018
He added a second Champions League winners’ medal in 2007/08, as a formidable side won three Premier League titles in succession and beat Chelsea in the first-ever all-English final in Moscow.
But for the brilliance of Barcelona and Pep Guardiola, he could have had even greater success after losing finals to the Catalans in both 2009 and 2011.