US Open 2019: Roger Federer's 5 most painful defeats at Flushing Meadows
Roger Federer endured his 14th defeat at Flushing Meadows, and his fourth from two sets to one up, as the Swiss maestro exited the 2019 US Open at the quarterfinal stage, losing for the first time in eight matches to Grigor Dimitrov.
Following his nemesis Novak Djokovic's exit in the fourth round, the opportunity was ripe for Federer to go all the way for a record sixth time at the US Open but Dimitrov had other ideas.
The defeat was Federer's fourth in 10 five-set matches at Flushing Meadows, and first against a player not named Djokovic or Juan Martin Del Potro.
Here is a look back at Federer's five most heartbreaking losses at the final Grand Slam tournament of the year.
#5 2019 Quarterfinals: Dimitrov beats Federer 3-6 6-4 3-6 6-4 6-2
In his 13th quarterfinal at Flushing Meadows, Federer faced world no. 78 Grigor Dimitrov of Bulgaria, a player he had beaten in each of the pair's seven previous meetings.
The winning streak looked set to continue as Federer rode an early break of the Dimitrov serve to take a one-set lead in under half an hour. Failing to capitalise on his momentum, the Swiss dropped serve at 2-3 in the second set, allowing Dimitrov to take a 5-2 lead.
Dimitrov failed to serve out the set at 5-3 as Federer broke back but the Bulgarian clinched the set when the Swiss failed to hold on to his serve in the next game.
Stung by the loss of a set to Dimitrov for only the third time in eight meetings, Federer broke the Bulgarian twice to take a two sets to one lead.
Dimitrov responded by breaking Federer in the first game of the fourth set. Federer survived a 12-minute service game at 2-4 by saving five breakpoints (three of them from 0-40 down) and looked set to get back on serve when Dimitrov stared at three consecutive break points when serving for the fourth set at 5-4.
However, he could not convert and Dimitrov took the fourth set. The missed opportunities would come back to haunt Federer, who left the court for a medical timeout. The Swiss then dropped serve in the opening game of the fifth and then again at 0-2 as Dimitrov took a commanding 4-0 lead.
Federer held his next two service games but was powerless to stop Dimitrov from closing out a 3-6 6-4 3-6 6-4 6-2 win.