#4 First player to win all the 9 Masters 1000 tournaments multiple times
Following five consecutive defeats in Cincinnati finals, Djokovic ended seven-time champion Roger Federer's perfect record in finals at the tournament by trumping the Swiss maestro in straight sets in the 2018 final. In the process, Djokovic became the first player to win the 'Career Golden Masters' - a term which describes the feat of winning each of the nine Masters 1000 tournaments at least once.
Though Federer and Nadal have also reached all nine Masters finals, Federer is winless from four finals in Monte Carlo and four in Rome, while Nadal is 0/5 in Miami finals, 0/2 in Shanghai finals and 0/1 in Paris-Bercy.
This year Djokovic came close to becoming the first player to win all nine Masters tournaments on multiple occasions when the defending champion led eventual winner Daniil Medvedev by a set in the Cincinnati semifinal, before going down in three.
With a title run at Cincinnati next year, Djokovic would complete unfinished business and create more history.
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