Roger Federer's 5 worst Grand Slam defeats

#3 Novak Djokovic (6-7 (9), 4-6, 6-3, 6-2, 7-5): 2011 US Open

2011 US Open - Day 13

The defeat that stung the most. Federer, seeded 3, had the top seed Novak Djokovic on the ropes as he raced out of the blocks, taking a two-set lead. The Serb though, as was his wont, struck back to level proceedings before running out of steam in the final set.

The Swiss cruised to a 5-3 lead and served for the match, bringing up two match points at 40-15. Djokovic though produced arguably the best return of serve in tennis history, slapping a forehand crosscourt for a clean winner. A visibly rattled Federer choked away another match point before double-faulting on break point to hand Djokovic a lifeline. The Serb did not lose another game as he held, broke and then held again to claim a 6-7 (9), 4-6, 6-3, 6-2, 7-5 victory.

Federer was clearly taken aback by the result and seemed to take a dig at Djokovic following the conclusion of the match, stating, “I mean, please. Some players grow up and play like that — being down 5-2 in the third, and they all just start slapping shots. I never played that way. I believe hard work’s going to pay off, because early on maybe I didn’t always work at my hardest. For me, this is very hard to understand. How can you play a shot like that on match point? Maybe he’s been doing it for 20 years, so for him, it was very normal. You’ve got to ask him.”

Not Federer's greatest moment by any means.