Williams' date night comes just two days after her U.S. Open final loss to 19-year-old Canadian Bianca Andreescu.
Dragan was one of a number of junior players practicing on Monday in the Royal City Tennis Club's competitive program.
"I could have just been more Serena today", the veteran tennis player said.
The veteran tennis star lost 6-3, 7-5, and previously lost to Andreescu during the 2019 Rogers Cup finals when Williams was forced to retire due to back spasms.
Ashleigh Barty has welcomed Bianca Andreescu's spectacular emergence as a threat to her world No.1 status and hopes the duo can forge a rivalry that endures for years to come. In her mission to become the best of any era, it may just be the end of an era for Serena, and a case of so near yet so far. "She has multiple strengths and uses them equally".
"I think you'll see enrollment probably go up", he said. It will be easier to maintain her ranking and even move up because she won't have any points to defend in the heart of next year's schedule.
"Pretty soon there will be a lot of Biancas out there", said Greenan.
"It hasn't really sunk in", Andreescu said on Live with Kelly & Ryan.
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"If she stepped on that court being a little intimidated by Serena, and not totally believing she could do it, she wasn't going to do it".
She was out of commission for nearly four months due to a shoulder injury, and suffered a bit of a groin strain during the Rogers Cup in Toronto but clearly recovered well enough to win the event and do what she did in NY.
"If I didn't do that, I'm sure Serena would have won that second set, so I'm really glad with how I handled everything". Steffi Graf won her final Grand Slam aged 30 and called it a day the same year. "She didn't get down on herself, even though I was ahead".
"It's been insane. I've been feeling all the love from home and I really appreciate it", she said on the Tonight Show, after which Fallon asked if there was anyone she hadn't heard from yet.
Le Graët : "Algérie-France s'éloigne"
Aulas en marge de l'assemblée générale de l'Association européenne des clubs qui se tient à Genève. Le président (de la Fédération Française de Football Noël Le Graët , ndlr) est pour.
Not long after the 2015 match, Palmer got married and retired as a professional tennis player.
The tennis pro said, "It's been insane, I've been feeling all the love from home". Watching Andreescu has been an inspiration.
"She has the ability, and my job was to help her make the most of the ability", said Bruneau. "It shows that hard work really pays off".
"She missed the clay-court and grass-court seasons and a lot of people thought the layoff would hurt her", said Bruneau.
US Open: Serena Williams, à une marche du record
Une grosse déception pour le Bâlois qui semblait pourtant sur une voie royale pour décrocher son sixième sacre à New York. Ce match avait duré moins de 20 minutes et a permis à Andreescu de remporter sa deuxième victoire de la saison en WTA.
"She doesn't give up", said Heyland.