A glorious career began with a crushing defeat

On 28 October 1995, Serena Williams’ professional career began with a crushing defeat. Her opponent retired just a few years later.

Serena Williams did not start her professional career with a bang, but with a heavy defeat. On 28 October 1995, the then 14-year-old lost 1–6, 1–6 to 18-year-old Annie Miller in the first qualifying round of the WTA tournament in Quebec City. Miller, also from the USA, was ranked 149th in the world at the time. The match lasted less than an hour.

For Williams, it was her first appearance at a professional event, having been groomed by her father Richard – much like her sister Venus – largely away from the junior circuit.

Serena Williams was “incredibly nervous”

A missed connecting flight in Philadelphia and her delayed arrival in Quebec City made her debut even more difficult – she was unable to train before the match. On a small side court, the expectations placed on the young American proved greater than her performance. “I was incredibly nervous. I just couldn’t cope with the nerves,” she later told tennis.com.

She said she had “played a bit like an amateur. I felt awful out there because I lost.”

The early exit did nothing to detract from her extraordinary career. Williams returned to the main WTA circuit in 1997 and, in Chicago, beat Mary Pierce and Monica Seles – then ranked number seven and four in the world – in succession.

Two years later, she won her first of 23 Grand Slam singles titles at the US Open and spent a total of 319 weeks at the top of the world rankings.

“It’s quite incredible that her and Venus’s careers have lasted so long and been so successful,” said Miller – who is now known as Annie Borus – on ESPN.

Williams’s opponent ended her career a few years later

Williams’ opponent, meanwhile, who attended the Nick Bolletieri Tennis Academy as a junior, reached a career-high of 40th in the WTA rankings in 1998 – and retired from the big tennis stage that same year at the age of just 21. Miller went on to study at the University of Michigan and later worked as an auditor, amongst other things.

“To be honest: even though Serena Williams would later go on to become the greatest of all time, I thought to myself: ‘I should definitely beat her, because I’ve been doing this for quite a while’,” said Miller. She simply wanted to improve her ranking, “so I just went out there and didn’t let the fact that I was playing Serena put me off; I just played my game”.

Referring to Williams’ first professional match, she added: “There was a lot of pressure on her. Back then, Venus was the one everyone was talking about.”

Williams retires – and returns in 2026

In August 2022, Williams announced the end of her playing career. At the US Open, she reached the third round, where she was defeated by Ajla Tomljanovic. In June 2026, Williams made a surprise return. Partnering Canadian Victoria Mboko, she won the doubles title in London and was then even awarded a wildcard for Wimbledon.

At the Grand Slam tournament, she suffered a 3–6, 7–6 (8–6), 3–6 defeat against the Australian Maya Joint. 28 October marks the anniversary of her first professional match.