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T2. Jose Mourinho - Two | 2004 (FC Porto) and 2010 (Inter Milan)
The jury is still out on where Jose Mourinho ranks among the greatest football managers of all time due to a decline in his output in recent years. However, one thing's for sure that he will go down as one of the most controversial managers of all time.
Mourinho displayed his impressive tactical knowledge and understanding of the game from the very beginning of his managerial career. He got his first big break with Porto, leading them to the Champions League title in his first season in-charge. In 2002-03, Mourinho led Porto to an unlikely triumph in the competition after beating mighty Manchester United in the last 16.
He has enjoyed a lot of success in the first decade of the century, winning multiple trophies with Chelsea and Inter Milan. The defining moment of his career came in 2009-10 when he guided a modest Inter squad to a treble, thanks to a win at all cost mentality and a no-nonsense defensive approach.
Mourinho has also added a Europa League trophy to his cabinet since with Manchester United in 2017, but he is often criticiced for his strategies which seem dated and ineffective in the current scenario.
T2. Pep Guardiola - Two | 2009, 2011 (FC Barcelona)
They say that the first impression is the last, and you will be judged by how you perform in your first job. Well, if that's the metric for football managers, Pep Guardiola has to get full scores for his incredible managerial debut with Barcelona in the 2008-09 season.
in 2009, Guardiola helped Barcelona complete a historic treble as the Catalan club won the Copa del Rey, La Liga and the Champions League. That form continued into the next season as the club won the Spanish Super Cup, the UEFA Super Cup and the FIFA World Club Cup.
That legendary side built around La Masia's golden generation - Lionel Messi, Andres Iniesta and Xavi Hernandez - won all six trophies up for grabs in 2010 and completed an unprecedented sextuple in the process.
Also Read: Lionel Messi net worth
In his four years at Camp Nou, Guardiola made it into the Champions League semifinals on each occasion, winning the competition in 2009 and 2011.
If we were to make a list of Champions League-winning managers based on the quality of wins rather than the quantity, Guardiola would be right at the top.
Also See: 5 Premier League managers with the best managerial start record.
