US Open 2019: Roger Federer's 5 most painful defeats at Flushing Meadows

#3 2010 Semifinal: Djokovic beats Federer 5-7 6-1 5-7 6-2 7-5

U.S. Open - Day 13

16-time Grand Slam champion Roger Federer faced familiar rival Novak Djokovic at the 2010 US Open semifinals. In each of their last three US Open meetings (2007 final, 2008 semifinal, 2009 semifinal), Federer had beaten the young Serb.

Federer's win streak against his newest rival at the last Slam of the year looked set to continue when the Swiss took a two sets to one lead. Djokovic took the fourth set to force a decider where Federer held two match points at 5-4 40-15 on the Serb's serve.

Djokovic hung tough to fend off the match points, broke serve for 6-5 and then held to seal the match.

The defeat ended Federer's run of six consecutive US Open finals as the Swiss was denied the opportunity of a first US Open meeting with his arch-rival Rafael Nadal.

It was the first time Federer lost a match at the US Open after having match points. It wouldn't be his last.