10 most painful Grand Slam defeats for Roger Federer

#7 2013 Wimbledon second round: Sergiy Stakhovsky beat Federer 6-7 (5), 7-6 (5), 7-5, 7-6 (5)

Stakhovsky stuns Federer in the 2013 Wimbledon second round

Unheralded 116th ranked Ukrainian Sergiy Stakhovsky served and volleyed his way to a stunning 6-7(5) 7-6(5) 7-5 7-6(5) victory as defending champion Federer suffered his first and till date only second round exit at a major. Following his earliest Wimbledon exit in eleven years since losing in straight sets to Mario Ancic in the first round in 2002, the Swiss tumbled out of the top four for the first time in ten years.

It was also the first time since the 2004 Roland Garros third round (lost to Gustavo Kuerten) that Federer failed to reach the second week at a major, ending an impressive streak of 36 consecutive quarterfinals. A difficult season would continue for the Swiss as he lost to Spaniard Tommy Robredo in the US Open fourth round, lost a second consecutive Basel final to Del Potro and lost to Nadal in the semifinal at the year ending ATP finals in London.