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Top 10 Managers of the Last Two Decades

A lifelong football fan trying to rank the masters of his favourite sport.

An inspiring man on the touchline is the cornerstone of nearly all major successes in football

An inspiring man on the touchline is the cornerstone of nearly all major successes in football

Since I started watching football two decades ago many great coaches appeared on the big stages of football, some went on and achieved great results. The great coaches of the last two decades often had different philosophies and methods with which they achieved their results, however, one thing that they most certainly had in common was that they had results. I am not going to lie, making this list was quite hard, I spent like two hours just brainstorming and writing down all the names, and their achievements. Writing down all the great names was the easier part, the second part was the trimming down of the list to just ten names, and then arranging the remaining ten into order. I tried to be as objective as possible, however as all football fans would know when it comes to our rivals and their managers, it is often impossible to put aside our biases.

I had some struggles deciding my method of selection also, at first I thought I will take into account the whole career of all the managers from this list, however, since I only started following the beautiful game from the 2001/02 season onwards, I decided to take into account only the periods I have seen myself, ai 2001/02 season to 2021/22 season period.

10. Arsene Wenger

Arsene Wenger was one of the truly great coaches of the world of football, his name for a time being was almost synonymous with Arsenal for me. I have witnessed just how good his Arsenal teams were when I started watching football as they won the 2001/02 and 2003/04 Premier League titles, the 2003/04 campaign they completed without losing a single game and for this achievement they are remembered now as „The Invincibles”.

Wenger also guided Arsenal to the Champions League final during the 2005/06 season, despite facing Frank Rijkaard’s incredible Barcelona and being a man down for most of the match Arsenal led Barcelona and it was only after the entrance of super-sub Henrik Larsson that Barcelona turned around the result. Once Arsenal built a new stadium and had to repay the loans Wenger also kept Arsenal for years in the Champions League and his young side fought for the league title in the 2007/08 season, a very impressive feat when one looks at the spending power of their rivals Chelsea and Man Utd.

Nonetheless, I felt that during his last 5-6 seasons Wenger started to deteriorate as a coach, his teams ran into big defeats more often and eventually even a part of the Arsenal fanbase started to share this opinion.

Overall Wenger won 2 league titles, 6 FA Cups, and 5 Community Shields during this period and was a no brainer for me to put him on the list.

9. Massimiliano Allegri

Allegri is one of the success coaches of the 2010s, he first coached Milan and after Antonio Conte’s surprise departure he took over the job at Juventus. Allegri just like Conte is known as a pragmatic coach, his teams may not play the beautiful football of Jurgen Klopp’s Liverpool or Pep Guardiola’s Man City, but they are very effective and ruthlessly get results.

Allegri had relatively little experience when he became the coach of Milan, but he quickly silenced his doubters and ended the stranglehold of Inter Milan over the Seria A by winning the title at the end of the 2010/11 season.

He failed to replicate this success in the following years against the resurgent Juventus of Conte, as Milan sold their best players and failed to replace them, their league performance became worse and worse each year, and Allegri finally left Milan in January 2014. His next job was at Juventus, an unhappy Conte left the team and Allegri was chosen as his replacement.

Allegri continued the domestic dominance of Juventus and improved the performance of the team in the Champions League, under his leadership Juventus reached the final of the Champions League twice, unfortunately for them losing both times. After winning five league titles in a row, Allegri left Juventus at the end of the 2018/19 season, however as Juventus had gone backwards since his departure he returned to them in the summer of 2021.

In total during his two stints at Milan and Juventus, Allegri had won 6 league titles, 4 Coppa Italia’s and 3 Supercups.

Allegri was linked with many Premier Leauge teams in the past few years before he rejoined Juventus this summer

Allegri was linked with many Premier Leauge teams in the past few years before he rejoined Juventus this summer

8. Antonio Conte

Conte is undoubtedly one of the very best coaches in the world of football right now, the demanding Italian has a proven track record of turning underperforming teams into champions and if I was a Tottenham fan right now I would feel optimistic about my team's chances of a good result this season.

Just like his compatriot Allegri, before receiving his first top job, Conte had relatively little experience, this did not stop him from reinvigorating Juventus when he became their coach. Before Conte’s arrival in 2011, Juventus finished 7th twice, under Conte’s guidance they became champions three times in a row. He left Juventus in the summer of 2014, when he felt the club’s hierarchy impeded him in taking Juventus to the next level, showing the one negative trait of Conte for me, his volcanic temperament and uncompromising nature, paired with his ability to simply walk away from jobs.

He next coached the Italian national team and took an unimpressive side to the quarter-finals of the Euro 2016, losing out on penalties against Germany.

His next job was at Chelsea, despite a rather unimpressive start to the season, his first season in England was a huge success. After a formation change to a back three, Chelsea were unstoppable and ran away with the title. His second season in London was more difficult, Conte was unhappy with the club’s transfer window before the 2017/18 season, Conte felt the club failed to sufficiently strengthen his squad before the season, he also fell out with some senior players during the season. All in all, Chelsea finished a disappointing fifth in the league, and despite winning the FA Cup Conte was sacked.

His next job was at Inter Milan, Conte took them from 4th to 2nd in his first season, in his second season Inter romped away with the title, however, thanks to the financial struggles caused by the pandemic the club was forced to sell some key players and Conte decided to leave.

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His current club is Tottenham Hotspur, after a difficult start Tottenham sacked their coach Nuno and turned to Conte to salvage their season, and who would bet against him?

Overall during his stints at Juventus, Chelsea and Inter Milan Conte had won 4 Italian league titles, 1 English league title, 1 FA Cup, and 2 Italian Supercups.


For each question, choose the best answer. The answer key is below.

  1. Who won the Champions League in 2014?
    • Sir Alex Ferguson
    • Carlo Ancelotti
    • Pep Guardiola
    • Jurgen Klopp

Answer Key

  1. Carlo Ancelotti

7. Diego Simeone

Before Diego Simeone’s arrival, Spanish football was dominated by Barcelona and Real Madrid, nobody came anywhere near them for years, some teams like Villareal, Valencia, Atletico Madrid, Sevilla were fighting to be the best of the rest. Nobody expected this situation to change with Simeone’s arrival, yet this is exactly what happened.

Simeone first made Atletico the best of the rest in the 2012/13 season by finishing third and winning the Copa del Rey against Real Madrid. The next season Atletico won the title ahead of the two giants of Spanish football and reached the final of the Champions League. After losing several key players Atletico had a weaker 2014/15 season, however, the next season they were back and reached another Champions League final and missed out the title by only three points.

Despite failing to repeat the Champions League performances of 2014 and 2016 Simeone kept Atletico in the top 4 in Spain and won a second title with them last season.

Simeone during his time at Atletico Madrid won 2 league titles, 2 Europa League, 1 Copa del Rey, 2 European Supercups and 1 Spanish Supercups.

Simeone put Atletico back on the map of the European Grandees

Simeone put Atletico back on the map of the European Grandees

6. Zinedine Zidane

Zidane is the rare case of a great footballer becoming a great manager also. Despite having a very short managerial career the achievements of Zidane are already numerous.

Zidane took over from Rafa Benitez halfway through the 2015/16 season, despite having a super squad Real Madrid was underperforming as the team failed to gel with Benitez. The situation instantly improved under Zidane and Real Madrid pushed Barcelona to the very end for the league title. More impressively Zidane won the Champions League with Real Madrid in his very first attempt.

He repeated his success the next season by winning another Champions League and this time Real Madrid also won the league title in Spain. Before the 2017/18 season, Real Madrid lost several important squad players like Alvaro Morata, James Rodriguez or veteran defender Pepe. Consequently, Zidane had a relatively weaker squad than the previous season and Real had a weak start to the season. Thanks to an impressive return to form in the spring Real won a third Champions League title in the row, however, thanks to the weak start they finished miles behind Barcelona in the league.

Zidane stepped down as Real boss at the end of the 2017/18 season only to return in March 2019. His second stint at Real was less impressive than his first, he succeeded in winning another league title, however Real failed to challenge for the Champions League. His degraders held his second stint as proof that it was the extremely strong Real squad and some questionable refereeing that was the decisive factor in his first stint rather than Zidane’s managerial genius. He stepped down from the bench of Real Madrid again this summer and is hotly rumoured as a target for French superteam Paris Saint-Germain.

During his short career so far Zidane had already won 2 league titles, 3 Champions League titles, 2 Spanish Supercups, 2 Uefa Super Cups and 2 FIFA Club World Cups.

Ancelotti has over two decades of experience ,and looking at the current season he still has plenty more to give

Ancelotti has over two decades of experience ,and looking at the current season he still has plenty more to give

5. Carlo Ancelotti

Ancelotti in his managerial career spanning over two and half decades had already managed half the great teams of Europe, this list includes Juventus, AC Milan, Chelsea, Paris Saint-Germain and Bayern Munich. As anybody could guess it is no coincidence that Ancelotti was chosen by all these great sides as the Italian is almost guaranteed to bring success.

Ancelotti achieved his greatest successes with AC Milan, he took over a struggling side in the autumn of 2001 and turned them into one of the best sides of Europe. Under Ancelotti’s guidance, they won the league title in the 2003/04 season, they also won two Champions League’s and reached the final another time. Unfortunately, Milan failed to reinvigorate their ageing squad after the Calciopoli scandal and Ancelotti finally left Milan in 2009.

Ancelotti inherited a brilliant, but slightly ageing squad at Chelsea. In his first season they edged out Man Utd for the title, Chelsea played some brilliant football under Ancelotti and broke the goal record of the Premier League. They also won the FA Cup beating Portsmouth in the final. His second Chelsea season started well also, however a bad run of form saw Chelsea drop from first to fifth, winter transfers failed to revitalise the squad and despite a stronger spring run Chelsea failed to overhaul Man Utd. Ending the season trophyless Ancelotti was sacked by Chelsea.

He joined PSG halfway into next season but failed to win the title, next season he won the league title with PSG. For next season he was signed to replace Jose Mourinho at Real Madrid, at Madrid he won the Champions League and the Copa del Rey in his first season, however, the injury of Cristiano Ronaldo in the spring of 2014 was probably just enough to cost Real the title. His second season with Real started well and they led the league standings, however, an off form Real in March lost the lead to Barcelona and never recovered. In the end, Real missed out on the title by 2 points and was eliminated in the semi-finals of the Champions League, Ancelotti was sacked after the season.

His next job was at Bayern where he won the league, however, after he fell out with several senior players he was sacked in his second season.

He next joined Napoli where he failed to challenge Juventus for the title, after Napoli he joined Everton where despite a positive start he failed to take them to the next level.

His latest job is at Real Madrid where he replaced Zidane, there is still much from the season left however so far Real look set to run away with the title.

During his long career, Ancelotti had won 4 league titles, 3 Champions Leagues, 1 Italian Cup, 1 Italian Supercup, 3 Uefa Super Cups, 1 Copa del Rey, 2 German Supercups and 2 Fifa Club World Cups.

4. Jose Mourinho

To be perfectly honest if I had written this article five years ago I may have just put Mourinho on the top of the list, however much has changed in the last five years and many experts and fans believe that Mourinho's career is in its twilight stages by now.

Mourinho burst into the biggest stages of football in the early 2000s like a rocket, he took Porto to two league titles, 1 cup, 1 UEFA Cup and most impressively to the Champions League title in 2004. Roman Abramovic lost no time and signed Mourinho for Chelsea in the summer of 2004. Mourinho won two league titles with Chelsea in his first two years in dominant fashion, in his third season he was edged out by a resurgent Man Utd. After a poor start to the 2007-08 season, he left Chelsea.

His next destination was Inter Milan, Inter dominated Italian football at the time however they failed to make an impression in the Champions League under Robert Mancini. Mourinho however was a different case, in his first season his team was barely any better than Mancini’s, in his second however they improved dramatically and won the Champions League, what made this victory even more impressive was the fact that they beat Ancelotti’s Chelsea, Pep Guardiola’s Barcelona and Louis van Gaal’s Bayern to clinch the title.

With his mission at Inter accomplished Mourinho was signed by Real Madrid, his next job was to topple Pep Guardiola’s Barcelona. He failed to achieve this in his first season and Real finished second to Barcelona, they were also eliminated by Barcelona in the semi-finals of the Champions League, beating Barcelona in the Cup final was small solace for Madrid fans. In his second season, Mourinho’s Real romped away with the title finishing nine-point ahead of Guardiola’s Barcelona. His third season at Madrid proved difficult, with Guardiola leaving many tipped Real to win another title however the teams league form was quite poor, they reached the semi-finals of the Champions League only to be beaten by Jurgen Klopp’s Dortmund.

In the end, Mourinho left Real with a disappointing final season.
He rejoined Chelsea and despite some positives failed to win a trophy in his first season, in his second season Chelsea walked away with the title and won the League Cup also. Many tipped them to retain their title however after a disastrous start to the season Mourinho was sacked in December.

He replaced Louis van Gaal at Man Utd next summer, however, despite winning a couple of trophies his Man Utd was barely an improvement over van Gaal’s, in his second season he improved the team’s league form but Pep Guardiola’s record-breaking City was just too strong for them. After an unimpressive transfer window and a bad start to the 2018/19 season, Man Utd sacked Mourinho in December.
He joined Tottenham next where he had an impressive start to the 2020/21 season, however as the season progressed their form faded and Daniel Levy sacked Mourinho only days before the League Cup final. He currently manages the Italian team AS Roma, a very good team still but one feels a step below the likes of Chelsea, Real Madrid or Man Utd.

All in all, Mourinho is one of the success coaches of the last two decades, in twenty years he had won 8 league titles, 2 Champions Leagues, 4 National Cups, 4 English League Cups, 2 UEFA Cup/Europa Leagues and 5 Super Cups.

3. Sir Alex Ferguson

To be honest as a Man Utd fan I have a very hard time putting Sir Alex below anyone, as I believe he is the greatest coach of all times, however, just looking in this period I felt that objectively I simply cannot put him on top.

Sir Alex’s name today is synonymous with Manchester United and he had spent the whole period at United. During this time Sir Alex won the title in 2002/03, however, he was forced to rebuild his team the next season and United wasn’t a serious title contender again until the 2006/07 season.

The Man United board’s patience with Sir Alex, however, was more than deserved as between 2006/07 and 2012/13(the last season of Ferguson) Man Utd won 5 out of the 7 league titles and finished marginally behind twice. United also won the Champions League in the 2007/08 season and reached the final two more times in 2009 and 2011. United also won 1 FA Cup, 3 League Cups, 5 Community Shields and 1 Fifa Club World Cups. All the more impressive was for me the fact that United won all these titles by playing the right type of football, as Sir Alex always felt that he had a duty to reward the fans with entertainment.

Besides the way his teams played football what amazed me about Ferguson was his incredible longevity, I am following the beautiful game now for 2 decades and I have seen numerous coaches who had their good periods but as time passed their football started to become outdated and they slipped from top coaches to merely good coaches.

According to some a similar process is happening now to Jose Mourinho, however nothing of the sort happened to Sir Alex who just before his retirement won the Premier League by a mile, finishing 11 points ahead of second-placed Man City. United also looked good in the Champions Leauge, in the last 16 United was leading Real Madrid 1-0 when a stupid red card allowed Madrid to turn things around and won the game 2-1, and get through to the quarter-finals with an aggregate score of 3-2.

The way Sir Alex was able to remain a top manager for over three decades almost defies logic

The way Sir Alex was able to remain a top manager for over three decades almost defies logic

2. Jurgen Klopp

Jurgen Klopp is widely regarded as one of the very best in the business, though if we just look at his list of achievements one might say that it is relatively unimpressive in comparison with some other names, however, if we take a deeper look we soon realise that Klopp’s achievements are as impressive as anyone else’s, if not more.

Klopp started his coaching career at second-division German team Mainz 05, under his guidance, Mainz won promotion to the top division of German football and stayed in the Bundesliga for a few seasons before being relegated to the second league again, after failing to win promotion during the 2007/08 season Klopp left Mainz.

Klopp joined struggling giant Borussia Dortmund, despite the financial troubles and poor results of the previous season Klopp instantly improved the team and finished 6th with them in his first season, in his second they improved to 5th.

Klopp then took Dortmund to two consecutive league titles in the 2010/11 and 2011/12 seasons, in latter Dortmund also won the cup after smashing Bayern Munich 5-2 in the final. In the following season, Dortmund failed to challenge Bayern Munich for the title, instead, they impressed the world by their superb run in the Champions League where they reached the final, in the semi-finals Dortmund defeated the Real Madrid of Jose Mourinho, only to came just short in the final where they were beaten by Bayern Munich. In his next two years, Dortmund's performance steadily dropped as they lost key men constantly and had bad luck with injuries also. After a disappointing final season, Klopp stepped down as manager of Borussia Dortmund.

He was not out of a job for long as Liverpool approached him in October 2015 to replace Brendan Rodgers, an offer Klopp accepted. Liverpool improved under Klopp however it was obvious for everyone that the team needed new players who were more suited to Klopp’s footballing philosophy. In his first season, he took Liverpool to the League Cup final and the Europa League final only to be beaten in both. In his second season, Klopp had the luxury of no European football and was able to concentrate on the league, where Liverpool had an impressive start but faded away in late Autumn and the winter months to finish in the end 4th.

The next season started quite badly and some were even questioning whether Klopp was even an improvement over Rodgers, the signing of Virgil van Dijk improved the team's defence and a much improved Liverpool reached the final of the Champions League and finished 4th. Goalkeeper Karius made several mistakes in the final against Real Madrid which cost Liverpool the match in the end.

Before the next season, Klopp signed goalkeeper Alisson Becker who helped to finally stabilise Liverpool’s defence. Liverpool had a great season and led the standings by 7 points before Man City went on a great run to overhaul them and just edge Liverpool for the title. In the Champions League Liverpool played in the same impressive fashion as in the Premier League, in the semi-finals they met Barcelona, in the first match they unluckily lost 3-0, only to turn the result around in a brilliant second leg victory. In the final, they met domestic rival Tottenham whom they edged 2-0 to win the big trophy.

Next season Liverpool romped away with the title and won it by a mile, in the Champions League they were favourites also however in a wasteful performance against Atletico they were eliminated in the last 16. In the 2020/21 season, Liverpool had horrendous luck with injuries plaguing their key players, with the absentees mounting up they failed to win any trophies. This season with the injury problems gone Liverpool looks to be back to their scintillating best and as things are standing at the moment are set to challenge for the league and the Champions League.

All in all, Klopp had won so far 3 league titles, 1 Champions League, 1 German Cup, 2 German Supercups, 1 Uefa Supercup and 1 Club World Cup, although this list is not as long as some others the fact that Klopp took over two struggling sides and turned them into champions for me it makes this list very impressive.

1. Pep Guardiola

Though it was not easy to pick the top spot in the end someone must be there too, and I feel it is simply impossible to overlook the success Guardiola had in the last decade and a half since his managerial career had begun at Barcelona.

When Guardiola took over in 2008 Barcelona had a brilliant squad, yet despite their superstar filled squad they failed to win a trophy in the last two years of the Rijkaard era. This changed under Guardiola who won three trophies in his first season, including the league and the Champions League. Before his second season, Barcelona swapped Samuel Eto’o for Zlatan Ibrahimovic, a mistake in hindsight because despite being a brilliant player Guardiola was unable to fit Zlatan into his system. Barca won the league title, but they were eliminated in the semi-finals of the Champions League by Jose Mourinho’s Inter.

Guardiola brought in David Villa to replace Ibrahimovic for the next season, the move worked and the front three of Messi, Villa and Pedro, with the midfield of Xavi, Iniesta and Busquets to back them up brought Barca another league title and another Champions League title also. His last season at Barcelona was less successful as Mourinho’s Real beat Barca to the title, and they also failed to win the Champions League after elimination in the semi-finals.

Guardiola took a year off and joined Bayern Munich for the 2013/14 season. At Bayern he won three league titles in a row, however disappointingly Bayern failed to reach the final of the Champions League after three consecutive elimination against Spanish teams(Real Madrid, Barcelona and Atletico Madrid). Guardiola left Bayern to become the manager of Man City.

Despite having endless funds Man City struggled to establish themselves as the dominant English team under Roberto Mancini and Manuel Pellegrini. Guardiola had a superb start to his first season, however, the defensive weakness of his team cost them many points and City dropped away from Chelsea in the standings. City was also quickly eliminated in the Champions League and failed to win any of the domestic cups.

Nonetheless despite an underwhelming first season, Man City’s owners backed Guardiola, with new signings improving the defence Man City ran away with the title in the 2017/18 season, and just edged Liverpool the next season. The 2019/20 season was more disappointing as City failed to challenge Klopp’s Liverpool and they had a shock loss against Lyon in the quarter-finals of the Champions League also.

The next season also started slowly for Guardiola’s City, it took him a quarter of the season to get his team firing, however, once City hit their form they were on fire and ran away with the title. They also finally reached the final of the Champions League and were favourites to win, in the end however Thomas Tuchel’s Chelsea edged Man City and won the big trophy. This season Guardiola’s City look devastatingly good so far, they dominated title rivals, Chelsea, in their away league game and at the moment I am writing this article are leading the league. They also topped their group in the Champions League and are among the favourites to win the competition.

All in all, Guardiola so far had won 9 league titles, 2 Champions Leagues, 5 National Cups, 4 English League Cups, 5 Super Cups, 3 Uefa Super Cups and 3 FIFA Club World Cups.

After contructing teams that dominated three of Europe's top leagues no one can doubt Guardiola by now

After contructing teams that dominated three of Europe's top leagues no one can doubt Guardiola by now

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2021 Andrew Szekler

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