Legendary encounters: WTA stars recall the excitement, fear of facing Serena
Photo illustration by Nick Roy / theScore

TORONTO - For any young player, a first-time matchup with Serena Williams can be overwhelming. In many cases, their date with the tennis legend is over before they know it.

Even Serena knows the feeling of being down and out early. In October 1995, a 14-year-old Williams officially began her professional career at the Bell Challenge in Quebec City. She would hold serve just once while falling 6-1, 6-1 to Annie Miller in the first round of qualifying.

"All I remember is I was incredibly nervous," Williams recalled at the Rogers Cup earlier this month. "I couldn't believe I was playing. I just couldn't deal with the nerves. It was a lot for me.

"I think I lost in like 30 minutes or something, and I just needed to go home and get a lot better. And then when I came back (17 months later), I was more ready to be able to play on the professional circuit."

Indeed, Williams returned from that humbling first match and became a superstar who transcends the sport. She's collected 23 Grand Slam singles titles - one away from Margaret Court's all-time record - while countless opponents on the WTA Tour have dealt with their own nerves upon seeing Serena on the other side of the net early in their career.

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Ukrainian Elina Svitolina and Australian Ashleigh Barty were both 17 years old and playing in front of their home fans when they first squared off against the future Hall of Famer.

Svitolina's turn came at the 2012 Fed Cup, where she was beaten soundly, 6-2, 6-1, in front of the European crowd. Barty met Williams for the first time at the 2014 Australian Open - a featured evening match to boot - and lost by the same score.

"Terrifying," Barty, this year's French Open winner, said of the experience. "It really was an incredible moment. But just being on the other side of the net to Serena for the first time was crazy. It was bizarre.

"I feel like I learned a lot from that match, and then having played her a year ago at the French (Open), I feel like it was a different match. But that’s all I try and do is learn from every experience."

Svitolina, who's now played Williams five times, finally broke through for a victory in the round of 16 at the 2016 Olympics.

"When you play against some great champions, it always gives you experience and the extra motivation to work hard to get another chance to play against them, and try to beat them," she said.

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Swiss star Belinda Bencic was also 17 when she met Williams for the first time, losing 6-2, 6-1 in the first round at the 2014 Madrid Open.

However, Bencic saw Williams again during her own breakout season in 2015. Williams entered their Rogers Cup semifinal in top form, having rolled through the tournament after winning the first three Grand Slams of that season.

It appeared Williams' dominance would continue after she claimed the first set, but Bencic battled back to win 3-6, 7-5, 6-4 - her first win over any player holding the world No. 1 ranking. Meanwhile, it was only Williams' second loss in 45 matches to that point in the year.

To this day, Bencic remembers "all the details." She had her serve broken at 5-3 in the second set and nearly squandered a 5-1 lead in the third. The experience tested her will, but it also proved that she possessed the intestinal fortitude to step up when it counts.

In her next match, Bencic topped Simona Halep to claim her first career WTA title.

"I think beating Serena, it's not about the tennis," she said. "It's about being mentally strong. Even if you're leading, you just have her in your head all the time."

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Current world No. 1 Naomi Osaka is one of a handful of players who own a winning record (2-1) against Williams.

Osaka first faced Serena as a 20-year-old at the 2018 Miami Open, and equated the experience to getting her hands on a fighting video game that she'd been eagerly waiting to try. Their first-round meeting was only Williams' fourth match after taking more than a year off to have her daughter, Alexis Olympia.

Still, the Japanese star also wanted to make a statement against Williams - her idol growing up - after winning her first career WTA title only a few days earlier at Indian Wells. And she did just that, seizing the opportunity with a 6-3, 6-2 victory.

"Every tennis player has that competitive edge where we want the chance to play her, and she's literally the best," Osaka said. "In tennis, I feel like if you want to prove something - especially if you’re young and coming up - you want to play the better players and you want to show them what you can do. For me, that was definitely the case when I played her."

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Rising Canadian star Bianca Andreescu went into her first matchup against Williams - the recent Rogers Cup final - with a similar attitude. Throughout her championship run in Toronto, the 19-year-old spoke about a "fearless" mentality she adopts on the court, and she didn't waver when it came time to face a legend.

While Williams' back spasms ended that final-round match early, Andreescu used their 19 minutes of competition to maximum effect, and led 3-1 when her opponent retired.

"Stepping on the court, I wanted to show her what I'm made of," Andreescu said after winning her second career WTA title. "But I try not to focus on that. I just want to put on the (best) performance for myself and for my team."

Former world No. 1 Caroline Wozniacki hadn't yet faced Serena or her sister Venus while coming up in junior tennis, but she still learned a harsh lesson from both of them - in an indirect way - about the elite level of play on tour.

When a young Wozniacki complained about hard serves from opponents, her father and longtime coach, Piotr, would tell her to "suck it up" because it wasn't as if Serena or Venus was hitting them.

Looking back, Wozniacki says that message helped overcome some early mental challenges. And when the Dane first played Venus in 2007 as a 16-year-old, she finally understood what her father had been talking about. The elder Williams sister won that meeting in Memphis by a 6-4, 6-4 scoreline.

Wozniacki has yet to find the ideal formula against Serena, with just a single win in 11 meetings (she's also defeated Venus only once in eight matches). But the 2018 Australian Open champion sees any opportunity to face the player she considers the "best ever" as the ultimate test.

"You always want to play the best players in the game and you want to have that experience to measure yourself up against them and know what you need to do to get there," Wozniacki said.

For her part, Williams is now a month away from turning 38 and nearing the twilight of her playing days. She's still undoubtedly focused on competition - even after winning 72 career singles titles and earning more than $90 million in prize money - but also on the long list of relationships that she's built through tennis. Wozniacki and Williams, for example, have developed a close friendship, and Williams served as one of Wozniacki's bridesmaids in June.

"It's really an extended family," Williams said. "You end up growing to have a lot of respect for all of these women out here that are traveling, working, and playing. You literally see them every week, week in, week out.

"And through that, I've met a lot of players. We get along. We hang out. We go to their weddings. It's really made me realize that these are lifelong friendships and experiences that so few people can have."

Up next for Williams is the US Open, which begins Monday in New York and will provide another chance to equal Court's all-time Grand Slam singles record - 20 years after Serena claimed her first at the 1999 edition.

"I love my job," she said. "I love what I do and I say this all the time, I feel really blessed and fortunate to have my career and my job. It's fun to be a part of an elite group of people that can go out and play in front of an amazing crowd.

"It's not much … longer that I’m going to do that," Williams added. "There's not many people that can do it, and so I'm just really proud to be a part of that."

Osaka, who will be the No. 1 seed in New York, also faced off against Williams in Toronto earlier this month, falling to her for the first time. There were moments in that match when the young star looked helpless and could do nothing but smile wryly to acknowledge a good shot from her opponent.

"This is how I thought the first time I played her in Miami was going to go," Osaka said afterward. "So in a weird way, (by) losing today I accomplished my dream. I know that sounds kind of weird, but if there's anyone in the world that I would want to lose to - of course I would never want to lose - I don't mind losing to her because I learned a lot.

"And this is someone that I kind of modeled my game after when I was little. So this is such a big learning experience for me."

Legendary encounters: WTA stars recall the excitement, fear of facing Serena
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