Roger Federer's 5 worst Grand Slam defeats

#2 Sergiy Stakhovsky (6-7 (5-7) 7-6 (7-5) 7-5 7-6 (7-5)): 2013 Wimbledon

The Championships - Wimbledon 2013: Day Three

Probably one of the biggest upsets of Roger Federer's career occurred in his favourite arena: Wimbledon's Centre Court in 2013. A whopping 113 places separated the two competitors, with Federer entering the tournament as the defending champion and World No. 3, and Stakhovski ranked No. 116.

However, the Ukrainian proved there was not much of a gulf in class, despite losing the opening set in a tight tie-breaker. He fought back to take the next 2 sets, 7-6, 7-5 and completed the monumental upset by claiming the fourth set tie-breaker as well, falling to the floor delirious in joy.

Stakhovsky's victory ended Federer's streak of 36 consecutive Major quarterfinals and represented his earliest loss at a Grand Slam since the 2013 French Open, where he had lost to Luis Horna.

The Ukrainian though would bow out soon after, succumbing to Jurgen Melzer in the next round.