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NEW YORK—It was nearly 11:00 p.m. on Wednesday night when Serena Williams took a familiar trip into Media Room 1 inside the USTA Billie Jean King Tennis Center. She had first entered this room as a teenager, back in the final years of the 20th century. Six times she’d conducted a press conference sitting alongside the trophy awarded to the women’s singles champion. On other occasions, she’d come in following a loss. And then there’d been so many post-match press conferences following routine early-round matches.

But now, at nearly 41, there was nothing routine about any aspect of Williams’ tennis. As she told me this evening, “I'm just pleased I showed up because the last few tournaments I didn't show up.”

This evening, for the second time in three days, Williams commenced a press conference following a match that had held the possibility of ending her singles career. And once again, she’d delayed that occurrence, earning a 7-6 (4), 2-6, 6-2 win over second-seeded Anett Kontaveit.

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Asked how it was to take on not just Williams, but a highly partisan crowd, Kontaveit said, “I expected it. You can expect something, I saw it from the previous match. When you're on the court, I mean, it was hard. I knew it was coming. Yeah, I guess you can't learn from anyone else's mistakes. Feeling it, it was something I never experienced before.”

Williams felt similarly: “I think you can only have this experience once in a lifetime, for sure.”

But of course, for Williams, it meant having as loud a cheering section as a tennis player can ever hope for—one of nearly 30,000 fans (a record night-match attendance in Arthur Ashe Stadium) that included an athletic icon whose journey and accomplishments are on par with hers: Tiger Woods.

“Yeah, he's one of the reasons I'm here, one of the main reasons I'm still playing,” said Williams. “So we talked a lot. He was really trying to get me motivated. There's a few people, but we were like, Okay, we can do this together, you know?

“It was good, because I didn't know what I wanted to do. I was just lost, so many questions. When you can rely on someone like that, I mean, my goodness, he's Tiger Woods, it was really helpful to get clarity.”

Tiger was seated near big sister Venus in Serena's players box on Arthur Ashe Stadium as the 23-time Grand Slam champion took on world No. 2 Anett Kontaveit.

Tiger was seated near big sister Venus in Serena's players box on Arthur Ashe Stadium as the 23-time Grand Slam champion took on world No. 2 Anett Kontaveit.

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Woods and Serena were both driven by fathers who expected them to become champions. Nearly 28 years ago, the week Venus made her debut in Oakland, Calif., in the back corner of a public court, Serena sat and watched her older sister. Turning to several of us, Richard Williams pointed to Serena and said, “That one’s going to be even better.”

And now, Serena has circled back to the beginning and found a way to relieve herself of any pressures.

“Yeah, I just feel like I have had a big red X on my back since I won the US Open in '99,” she said. “It's been there my entire career, because I won my first Grand Slam early in my career. But here it's different. I feel like I've already won, figuratively, mentally. It's just pretty awesome the things that I've done. I never, like, accept that. I never think about it.

“Yeah, so tonight I was just like, Serena, you've already won, just play, be Serena. You're better than this.”

"I feel like I've already won, figuratively, mentally," said Serena after her second-round win. A freed-up Williams is a dangerous thing for her opponents.

"I feel like I've already won, figuratively, mentally," said Serena after her second-round win. A freed-up Williams is a dangerous thing for her opponents.

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Asked to assess her tennis tonight, having now won 108 singles matches at the US Open, Williams said, “I'm playing pretty good. I feel, like I said on the court, I've been practicing really well, but it hasn't been coming together in matches. But, you know, now it's kind of coming together, I guess. I mean, I had to bring it together today. It worked out.”

This is how it goes in tennis: You start out simply playing. Then you enter a world of competition, of results and expectations and potential outcomes. But then, at another stage, you’re once again merely playing.

“Yeah, I feel like everything is a bonus. Like, it's that weird mixture of embracing but also staying focused,” she said. “So I'm just really trying to figure out which percentage I want of each.”

We’ll learn more on Friday, when she takes on Australian Ajla Tomljanovic.