10 most painful Grand Slam defeats for Roger Federer

#5 2010 US Open semi finals: Djokovic beat Federer 5-7 6-1 5-7 6-2 7-5

Djokovic saved 2 match points against Federer to reach first US Open Final

Then 16-time Grand Slam champion Federer faced familiar rival Djokovic at the 2010 US Open semis. The Swiss had beaten the young Serbian in each of their last three US Open meetings (2007 final, 2008 semifinal, 2009 semifinal).

Federer's win streak against his new rival at the last Slam of the year looked set to continue as the Swiss took a two sets to one lead. The match proceeded to a deciding set where Federer held two match points at 5-4 40-15 on the Djokovic serve.

Djokovic, though, hung tough to fend off the match points, held serve for 6-5 and broke the Swiss in the following game. Defeat ended Federer's streak of six consecutive US Open finals as the Swiss was denied the opportunity of a first US Open meeting with his arch rival Nadal.