Serena Williams and Grigor Dimitrov are known to be close friends. The former was in attendance at the US Open to watch the Bulgarian survive a scare from Andrey Rublev and reach the quarterfinals of the New York Major
This is Dimitrov’s first last-eight appearance in Flushing Meadows since 2019 when he reached the semifinals.
There have been a few occasions when Williams was present to cheer the Bulgarian, who is a good friend of hers as well as her sister Venus. The 23-time Grand Slam champion and Dimitrov have often spoken fondly of one another.
So, without any further ado, let’s take a look at five such instances:
#5 “It’s friendship, man, I think this is the best part” – Miami Open 2024
Serena Williams was in attendance at the Miami Open this year to watch the men’s singles semifinals. Grigor Dimitrov was in action, as he faced Alexander Zverev. The Bulgarian beat the German 6-4, 6-7(4), 6-4 to reach the final.
After his win, Dimitrov said of Williams:
“She’s amazing. We stay in touch. We nearly speak on a daily basis. She said, I’m gonna come watch. I was like, Okay. It’s always very humbling to have such a supporter in your corner, and I think just before the match she came, we had a little chat.”
“Actually, I remember she was even here when I had my first top-10 win. It was a very nice moment. I think we both remember that. It’s friendship, man. I think this is the best part.”
#4 “Love you Grigs” – Serena Williams to Grigor Dimitrov after the Bulgarian’s Paris Masters 2023 run
Grigor Dimitrov had a remarkable run at the 2023 Paris Masters, reaching the final following wins over Lorenzo Musetti, Daniil Medvedev, Alexander Bublik, Hubert Hurkacz, and Stefanos Tsitsipas.
Here, the Bulgarian faced Novak Djokovic and lost 3-6, 4-6. After the tournament, Dimitrov took to Instagram and posted a video that had a message of thank you from him to his fans and well-wishers. Venus Williams commented by joking that she was the Bulgarian’s biggest fan ahead of Serena Williams
“Please note I am your biggest fan more than Serena Williams.”
Dimitrov responded to this by saying:
“Aiii aiiii what will Serena Williams say now?!”
The 23-time Grand Slam singles champion responded, saying:
“Love you Grigs”
#3. “They are such amazing humans” – Grigor Dimitrov on Venus and Serena Williams in 2022
Grigor Dimitrov reached the quarterfinals of the BNP Paribas Open in Indian Wells in 2022 with a 6-3, 7-6(6) win over then-23rd seed John Isner in the fourth round. Venus and Serena Williams were both in attendance to watch him play.
Speaking after the match, Dimitrov initially joked that there was a lot of pressure playing in front of the Williams sisters before calling them “amazing humans” and said:
“So much [the pressure when Venus and Serena Williams are watching him play]. No, definitely not. You know, they are such amazing humans, I share such a great relationship with them and I am so thankful, I am grateful every time they come and cheer me up.”
#2. “I love your style, thanks to me, of course” – Grigor Dimitrov’s letter to Serena Williams in 2021
During the 2021 Cincinnati Open, Grigor Dimitrov appeared in a video where he had to send a complimentary letter to someone from the WTA Tour and he picked the younger Williams sister.
““So I’m doing this press over here, I had to write a complimentary paper to someone from the WTA so I figured you because I love your style so much, and here it goes,”
Dimitrov said.
The Bulgarian then jokingly said he was responsible for her playing style.
“I love your style, thanks to me, of course.”
#1. “Serena gave me a good prep talk” – Dimitrov reaches US Open quarterfinals with the American in attendance
Williams was in Flushing Meadows to watch Grigor Dimitrov and Andrey Rublev play in the fourth round of the 2024 US Open. The Bulgarian emerged victorious, winning 6-3, 7-6(3), 1-6, 3-6, 6-3 to reach his eighth Grand Slam quarterfinal.
After the match, the World No. 9 said that Williams gave him a good pep talk the day before.
“She gave me a good prep talk yesterday. Yeah, I know exactly, I’m thrilled, it’s amazing to play again in front of you guys, in front of friends and family. So all in all, it’s a tremendous atmosphere here, so thank you for the support,” Dimitrov said.
The Bulgarian will next face 20th seed Frances Tiafoe in the US Open quarterfinals, with the winner facing either fourth seed Alexander Zverev or 12th seed Taylor Fritz.