Novak Djokovic leads the Tour with 38 Masters titles to his name. He remains the only player to have won all 9 Masters events atleast once although he has won all 9 titles twice.
Rafael Nadal sits second on the list with 36 Masters titles to his name. Apart from Djokovic, he is the only other man to have won more than 30 Masters titles.
Roger Federer
Roger Federer is third on the list with 28 Masters titles. Similar to Nadal, he has won 7 of the possible 9 Masters events and is only one of the three men with more than 20 Masters titles.
Andre Agassi held the record for quite some time with his 17 titles before Federer eclipsed him. Similar to the Swiss maestro, he has won 7 of the 9 events.
Andy Murray completes the Top 5 with 14 Masters titles to his name. Barring Djokovic, similar to the rest, he has also won 7 of the 9 Masters events showing surface wide adaptability and skill.