A tearful Serena Williams admitted to feeling "a lot of emotions" as she was beaten in straight sets by Belinda Bencic in Toronto.
Williams, playing her first match since announcing her imminent retirement from the sport, lost 6-2 6-4 to the Swiss to exit the Canadian Open at the second round stage.
The 23-time Grand Slam winner, widely regarded as the greatest player of all time, revealed in an interview with Vogue magazine this week that she was "evolving away" from tennis and is "ready for what’s next".
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"It was a lot of emotions, obviously," she said in her on-court interview after the loss, as she wiped away a tear. "I love playing here, I've always loved playing here.
“I wish I could have played better but Belinda played so well today. It's been an interesting 24 hours.
"As I said in the article, I'm terrible at goodbyes. But, goodbye Toronto."
She added: "I was really happy to be out here today and play in front of you guys, thanks for the support."
The 40-year-old is expected to bow out after this summer’s US Open but her preparations for the Grand Slam event suffered a blow with this defeat.
Williams was on the back foot from the start, having to save two break points in her opening service game, but was ultimately broken twice before Bencic claimed the first set on her fifth set point.
Williams showed more resistance in the second set but eventually lost her serve for 4-3 and then went long with a forehand on match point to hand the Tokyo 2020 gold medallist the win.
Speaking afterwards, Bencic paid tribute to Williams on an amazing career.
"Of course, it's super nice, but today it's a little bit more sad in a way,” she admitted.
“I don't really want her to retire. I feel like I've always, in a way, you know what she's achieved and everything, all her legacy and career and everything. But now that it's soon to be over I feel like people, and me included, are realising it even more.
"Just standing on the court against her today was just, yeah, really overwhelming, I would say."

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She added: "In a way with her it feels almost like I'm star struck every time I see her, so it's difficult to play her.
“It's difficult to kind of put that aside and just like focus on the match. Because I feel like I just don't know how I then play because I feel like I'm paralysed a little bit just like watching her.
"The crowd was incredible tonight. Just being part of that whole thing, it's just really very special for me as well and for her. And I think the US Open, it's going to be even more special. So good luck to everyone who has to play her."
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