Throughout the year, there were upsets that shocked fans and players alike, matches that made the world go "Wait...who won?!" Let's take a look back at the Top 10 biggest upsets of 2019.

4

Setting: US Open, quarterfinals

Rankings: No. 78 vs. No. 3

Head-to-Head: 0-7

This year's US Open was the tournament for upsets. Dimitrov, who once upon a time was called "Baby Fed" due to their similar play styles, took on Federer in their eighth career meeting, in New York. The 28-year-old was a significant underdog, having never beaten the Swiss even once.

After a quick 25-minute first set, the match was seemingly going to be like any other between the two: a quick win by Federer. But, something switched in Dimitrov and what was supposed to be a simple victory became a drawn-out war, culminating in a five-set win for the Bulgarian, 3-6, 6-4, 3-6, 6-4, 6-2.

Top 10 upsets of
2019: No. 4, 
Dimitrov def. Roger

Top 10 upsets of 2019: No. 4, Dimitrov def. Roger

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It was also the first time in his career that Federer lost to someone at the US Open ranked outside of the Top 60.