# 200th win: 2009 Indian Wells Round of 64
Djokovic arrived at Indian Wells 2009 fresh off winning his 12th singles title, in Dubai. The Serb launched his title defence in the desert with a straight-sets win over Argentine Martin Vassallo Arguello.
In a hard-fought match, Djokovic beat Vassalo Arguello 7-5 6-4 to record the 200th match win of his singles career. The Serb would, however, fall to American Andy Roddick in straight sets in the quarterfinals.
# 300th win: 2010 Cincinnati Round of 32
Making his sixth appearance in Cincinnati, returning two-time finalist Djokovic conquered countryman Viktor Troicki 6-3 7-5 to open his campaign on a winning note.
That marked the 23-year-old's 300th career singles win. Djokovic would go on to lose in the quarterfinals to Andy Roddick - one of the few players who can boast of a winning head-to-head record against the 16-time Grand Slam champion.
# 400th win: 2012 Australian Open semifinals
Defending champion Djokovic met his match against an inspired Andy Murray in the 2012 Australian Open semifinals.
In a repeat of the pair's 2011 title match, Djokovic took the opener but found himself trailing by 2 sets to 1 as Murray grabbed the third set on a tiebreak.
The reigning world number one raised his level to take the fourth set 6-1. And despite a late Murray fightback from 2-5 down in the decider, the Serb went on to reach his third Australian Open final - where he would conquer Rafael Nadal in another five-set epic to successfully defend his title.
# 500th win: 2013 Roland Garros Round of 32
Having split their two previous meetings earlier in the season, with Djokovic beating Grigor Dimitrov at Indian Wells and the Bulgarian returning the compliment in Madrid, the pair met again in the third round at Roland Garros 2013.
In his first Grand Slam meeting with Dimitrov, Djokovic emerged a 6-2, 6-2, 6-3 victor. The win was Djokovic's 500th in singles play on the ATP tour.
The Serb would go on to squander a break lead in the deciding set of the semifinal against three-time defending champion Rafael Nadal.
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