10 most painful Grand Slam defeats for Roger Federer

#3 2009 Australian Open final: Nadal beat Federer 7-5 3-6 7-6(3) 3-6 6-2

A fifth Grand Slam final defeat to Nadal reduced Federer to tears at the 2009 Australian Open

Following a difficult 2008 season, by Federer's standards, after two debilitating defeats against Nadal in the finals of the French Open and Wimbledon, Federer arrived at the 2009 Australian Open hoping to equal Pete Sampras' then record tally of 14 Grand Slams.

Heartbreak awaited the Swiss as Nadal reeled off consecutive five-set wins in as many days (beat Verdasco in the semis) to deny Federer a shot at history. After a fifth reverse in a Slam final against his Spanish nemesis, the defeat was so debilitating and deflating for the Swiss that he was reduced to tears at the trophy ceremony. In a magnanimous gesture, Nadal hugged his good friend Federer on court and assured him that a 14th wasn't far away. The words proved prophetic enough as the Swiss reached the magical figure, with his first French Open title, few months later.