Overall, Djokovic has a record of 188-51 with 14 titles in these Masters Series 1000 events. He won his first in just his 11th try at the 2007 tournament in Miami. Later that year, Djokovic claimed the title in Canada with his first career win against Roger Federer.
As the Serb, began his 2008 season, he showed that he was ready to compete at the top level of the sport. Following his first grand slam title, Djokovic defeated Mardy Fish for the title at Indian Wells. The emerging star claimed his fourth Masters Series title at a different event in Rome. Djokovic also reached the Cincinnati final for the first time, losing in two tiebreak sets to Andy Murray.
It was in 2011, when Djokovic became one of the most dominant players at the Masters Series 1000 events. The Serb won all of the first five events of the series that he played in on his way to becoming the No. 1 player in the world. His title in Madrid, where he beat Rafael Nadal in straight sets, pushed his total to six different titles. His five titles in one season is the record for most won in one year.
Djokovic has now won nine of the last 24 Masters Series titles since the start of the 2011 season. In 2012, the Serb saved five championship points in the second set against Andy Murray in Shanghai as he came back to win the title for the first time.
Coming into this year, Djokovic was missing just two titles from completing the Super Nine Sweep, which was by far the closest any player has come. In Monte Carlo, he elected to play the event despite having an ankle injury. After struggling to get past the first two rounds, he routed Rafael Nadal in the final, ending the Spaniards eight-year undefeated stretch and claiming the title for himself for the first time. After the match, Djokovic said it was the best decision of his career so far to play in the tournament.
Now Djokovic enters Cincinnati, which is the only tournament missing from his collection of Masters Series titles. He plays his first match on Wednesday against Juan Monaco. The Serb enters the tournament with a great chance of reaching the final for a fifth time in his career. Djokovic has just Juan Martin Del Potro on his side of the draw that presents a serious threat. After that, he could meet Nadal, Federer, or Murray in the final for a chance to complete the Career Masters Slam.