The 23-time Grand Slam champion was defeated 6-2, 6-4 by Belinda Bencic in the second round of the Canadian Open in Toronto – her first match since penning an article in Vogue explaining, that “the countdown has begun” and that she will “evolve away from tennis”.
“Like I said in the article, I’m terrible at goodbyes. But goodbye Toronto,” she said in an on-court interview after the game.
It was likely Williams’ last appearance at the Canadian Open, having won the tournament twice during her incredible career.
Along with her older sister Venus, she helped transform the sport by regularly winning Grand Slams in both singles and doubles tennis.
The 40-year-old has amassed 73 singles titles, 23 doubles titles and two mixed doubles titles, including 39 Grand Slam titles – 23 singles titles, 14 doubles titles and two mixed doubles titles.
“There were a lot of emotions, of course,” Williams told the crowd, speaking about the game.
“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.
“Anyway, that’s it. I was really happy to be out here playing in front of you guys today, thanks for the support.”
Fans crowded into the 12,500-seat stadium to watch William’s farewell, and tournament organizers set up, for the first time ever, an outdoor viewing area that could seat an additional 5,000 spectators.
Inside the stadium, the crowd held up signs that read, “Thank you, Serena,” “23, we’ll miss you,” or simply “Queen.”
A farewell presentation ended with Williams accepting a gift from the Toronto Maple Leafs of the NHL and the Toronto Raptors of the NBA.
Williams is expected to play next at the Western and Southern Opens in Cincinnati, followed by the US Open, which she says will be her final tournament.
Meanwhile, on Wednesday, Coco Gauff defeated Wimbledon champion Elena Rybakina 6-4, 6-7(8), 7-6(3) in a marathon match lasting 2 hours and 49 minutes to move into the last 16.
Nick Kyrgios also moved into the last 16 with an impressive 6-7(2), 6-4, 6-2 win over world No. 1 Daniil Medvedev.
CNN’s Ben Morse contributed to this report.