I was the first player to ever beat Serena Williams in a professional tennis match but then I retired at the age of just 21

Serena Williams is, of course, a legendary figure in tennis and sports in general, but she didn’t have the dream debut that many of her peers enjoyed.

Williams misses tennis ‘like crazy’, with the 23-time Grand Slam champion having retired after her third round US Open exit in 2022. The former number one won a stunning 73 titles during her career, with her Grand Slam total behind only Margaret Court’s 24 in the women’s game.

But overall, only Novak Djokovic (24) has more than Williams, with the latter ahead of the likes of iconic figures Roger Federer and Rafael Nadal. Like many players that have come before and indeed after her, the American burst onto the scene as a teenager. But her career began earlier than most, with a 14-year-old Williams debuting on the WTA Tour in a qualifying match at the Bell Challenge in 1995.

Quebec City hosted the WTA Tier III event in late October, with the future superstar drawn to face Annie Miller. And it was Miller who emerged victorious, with the world number 149 overcoming young talent Williams 6-1, 6-1. Serena failed to follow in the footsteps of her sister Venus Williams with the loss, with the latter beginning her career a year earlier with a win in Oakland.

Bollettieri Academy graduate Miller will always have her place in history, with not a lot of players able to overcome future world-beater Williams. The former was just 18 when she met the 14-year-old rising star, but that age gap and her experience on the court ensured she was full of confidence going into the match.

“I remember about Serena Williams that she and Venus were coming onto the scene,” Miller told MLive in 2018 Venus had already been having some success in pro tournaments, and everyone knew that Serena was going to be the next sister to come on to the tour.

“However, at that time, I had already been playing some professional tournaments, and I was also fairly young at the time, so in my mind, I thought I had every shot of winning the match, so I went out there with a little more experience than she had at the time, and played a good match, won the match. And I thought that was just another day at the tennis courts, but little did I know that over 20 years later, it’s sort of become the thing that people like to talk about when they ask me about tennis.

“For me it’s a good sound bite, but I would of course want to say it was an incredible experience and I’m proud to say that I did play Serena, and of course in awe of everything she’s achieved and what she’s done for the sport and for kids and for everyone around the world.”