Williams' total of 23 Grand Slam singles titles is more than any woman in the Open eraAn emotional Serena Williams has admitted she is "terrible at goodbyes" following defeat by Belinda Bencic in the second round of the Canadian Open.
The 23-time Grand Slam champion lost 6-2 6-4 in Toronto in her first match since announcing she will be "evolving away" from tennis.
The American, 40, received a standing ovation on court and had the full backing of the crowd throughout.
"It was a lot of emotions obviously," said Williams.
"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."
Writing for Vogue on Tuesdayexternal-link, Williams said she was moving towards "other things that are important to me", adding she did not like the word "retirement".
In an accompanying Instagram postexternal-link, she wrote that "the countdown has begun".
Following the match, a tearful Williams was presented with jerseys of basketball team the Toronto Raptors and ice hockey team the Toronto Maple Leaves for her and daughter Olympia.
"I was really happy to be out here today and play in front of you guys," she said. "Thanks for the support. Thank you."
Williams won her first Grand Slam title at the 1999 US Open, aged 17. Her last Grand Slam title was at the 2017 Australian Open when she was eight weeks pregnant with Olympia.
She has confirmed she will play at the Western and Southern Open in Cincinnati, Ohio next week as well as at the US Open later this month.
Serena Williams is the reason I play tennis - Coco GauffSwiatek and Gauff through to last 16
World number one Iga Swiatek will join Switzerland's Bencic in the third round after comfortably beating Ajla Tomljanovic 6-1 6-2.
The two-time Grand Slam-winner, 21, will face Brazil's Beatriz Haddad Maia next.
The victory was the Pole's 19th successive hard-court win.
American Coco Gauff beat Wimbledon champion Elena Rybakina 6-4 6-7 (8-10) 7-6 (7-3) to set up a meeting with Belarusian Aryna Sabalenka, but Estonia's second seed Anett Kontaveit is out after losing 6-4 6-4 to Switzerland's Jil Teichmann.
