BREAKING….I was the first player to ever beat Serena Williams but retired at 21 despite top-50 world ranking to switch careers

Serena Williams kicked off her illustrious career with a loss.In her professional debut, she lost to Annie Miller in straight sets, but after that, the pair went on to have wildly different careers.Back in October 1995, in a qualifying round of a late-season tournament in Quebec City, a 14-year-old Williams took on Miller, 18, in a game that went exactly as expected.That was a dominant 6-1, 6-1 win for Miller as, with Williams four years her junior and relatively unknown, there not much to worry about from the young American.
The game was the worst possible pro start for Williams, who was making her professional debut, something she reflected on in 2015.
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I was the first player to ever beat Serena Williams but retired at 21 despite top-50 world ranking to switch careers
Mohamud Ahmed
8th November 2025, 3:16 pm
Updated: 8th November 2025, 3:17 pm

Serena Williams kicked off her illustrious career with a loss.

In her professional debut, she lost to Annie Miller in straight sets, but after that, the pair went on to have wildly different careers.

er being defeated by Ajla Tomlijanovic of Australia during the Women’s Singles Third Round match at the USTA Billie Jean King National Tennis Center during the day 5 of the 2022 U.S. Open Tennis Tournament on September 2, 2022. In New York.
GETTY
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Serena Williams’ professional career began with a defeat

Back in October 1995, in a qualifying round of a late-season tournament in Quebec City, a 14-year-old Williams took on Miller, 18, in a game that went exactly as expected.

That was a dominant 6-1, 6-1 win for Miller as, with Williams four years her junior and relatively unknown, there not much to worry about from the young American.

The game was the worst possible pro start for Williams, who was making her professional debut, something she reflected on in 2015.
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“Basically she crushed me,” Williams said. “Not only did I look like a novice but I looked like I did not belong anywhere on the court.

“I didn’t play like I meant to play, I played kind of like an amateur.”

That loss would then see Williams not play another professional game for three years as her father Richard Williams, didn’t believe she was ready.

Nevertheless, the game, despite being played on a indoor carpeted court at Quebec City’s leisure centre, would end up becoming one of tennis’ famous matches.Not least because Williams went on to become the most successful female singles player in the Open Era with 23 Grand Slams, but also because Miller would end up quitting the sport at 21.

Miller reached a career high ranking of 43rd in the world but still decided to leave the sport at such a young age to pursue an education.

The former young tennis star went to the University of Michigan to complete her bachelor’s in business administration and later a master’s degree in accounting.Talking to ESPN back in 2015, Miller reflected on the decision that she describes as extremely difficult.

“It was a hard stop for me,” Miller says. “I was so young, I spent years looking back on it, wondering if I made the right choices.

“Mentally, I feel it would’ve been so good for me to see what was out there in the world, and that there is more to life than tennis.”Now, Miller, who has worked as an accountant for a sports marketing firm and for Adidas, is a stay-at-home mum in Portland and on the board of directors for a local non-profit.

Miller maintains that she is grateful for the way her life has turned out but has gained more perspective on tennis, which had her moving on her own to Florida to train at the Bollettieri Academy at age 15.

“At the time, it was such a young sport. You had to get out there at 16 and win and turn pro and solider on, she said.
I was the first player to ever beat Serena Williams but retired at 21 despite top-50 world ranking to switch careers
Mohamud Ahmed
8th November 2025, 3:16 pm
Updated: 8th November 2025, 3:17 pm

Serena Williams kicked off her illustrious career with a loss.

In her professional debut, she lost to Annie Miller in straight sets, but after that, the pair went on to have wildly different careers.

er being defeated by Ajla Tomlijanovic of Australia during the Women’s Singles Third Round match at the USTA Billie Jean King National Tennis Center during the day 5 of the 2022 U.S. Open Tennis Tournament on September 2, 2022. In New York.
GETTY
4
Serena Williams’ professional career began with a defeat

Back in October 1995, in a qualifying round of a late-season tournament in Quebec City, a 14-year-old Williams took on Miller, 18, in a game that went exactly as expected.

That was a dominant 6-1, 6-1 win for Miller as, with Williams four years her junior and relatively unknown, there not much to worry about from the young American.

The game was the worst possible pro start for Williams, who was making her professional debut, something she reflected on in 2015.
Advertisement

“Basically she crushed me,” Williams said. “Not only did I look like a novice but I looked like I did not belong anywhere on the court.

“I didn’t play like I meant to play, I played kind of like an amateur.”

That loss would then see Williams not play another professional game for three years as her father Richard Williams, didn’t believe she was ready.

Nevertheless, the game, despite being played on a indoor carpeted court at Quebec City’s leisure centre, would end up becoming one of tennis’ famous matches.
Advertisement

Not least because Williams went on to become the most successful female singles player in the Open Era with 23 Grand Slams, but also because Miller would end up quitting the sport at 21.

Miller reached a career high ranking of 43rd in the world but still decided to leave the sport at such a young age to pursue an education.

The former young tennis star went to the University of Michigan to complete her bachelor’s in business administration and later a master’s degree in accounting.

Serena Williams went on to forge one of the most remarkable careers
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Serena Williams went on to forge one of the most remarkable careers
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Serena Williams won the US Open in 1999, just four years after making her pro debut at 14
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Serena Williams won the US Open in 1999, just four years after making her pro debut at 14

Talking to ESPN back in 2015, Miller reflected on the decision that she describes as extremely difficult.

“It was a hard stop for me,” Miller says. “I was so young, I spent years looking back on it, wondering if I made the right choices.

“Mentally, I feel it would’ve been so good for me to see what was out there in the world, and that there is more to life than tennis.”
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Now, Miller, who has worked as an accountant for a sports marketing firm and for Adidas, is a stay-at-home mum in Portland and on the board of directors for a local non-profit.

Miller maintains that she is grateful for the way her life has turned out but has gained more perspective on tennis, which had her moving on her own to Florida to train at the Bollettieri Academy at age 15.

“At the time, it was such a young sport. You had to get out there at 16 and win and turn pro and solider on, she said.

Serena Williams crowns Keely Hodgkinson with a Tiffany tiara
Getty
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While Williams has been retired for two years, she remains the greatest female tennis player
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“By 18, I felt like ‘I’ve been at this a long time already’. It was such a grind.

“But now I look at Serena in her early 30s and I wish I would’ve known [it was possible to play that long]. It is pretty incredible, though, that she and Venus’ careers have endured so long and been this successful.”

Both Williams and Miller no longer play tennis anymore and while the former went on to win 73 WTA titles, the pair have both publicly reflected on the great careers they’ve enjoyed.