There was a german player named karsten braasch. An he played against serena (and maybe venus too...dont remember the story).
Braasch was drunk and smoking during the changeovers (as he tells the story). He played both Williams sisters in succession in 1998 in Melbourne and beat Serena 6–1 and Venus 6–2. Braasch was thirty years old at the time, while Venus and Serena were seventeen and sixteen, respectively.
As Wikipedia describes it:
Venus and
Serena Williams had claimed that they could beat any male player ranked outside the world's top 200, so Braasch, then ranked 203rd, challenged them both. Braasch was described by one journalist as "a man whose training regime centered around a pack of cigarettes and more than a couple of bottles of ice cold
lager".The matches took place on court number 12 in
Melbourne Park, after Braasch had finished a round of golf and two shandies. He first took on Serena and after leading 5–0, beat her 6–1. Venus then walked on court and again Braasch was victorious, this time winning 6–2. Braasch said afterwards, "500 and above, no chance". He added that he had played like someone ranked 600th in order to keep the game "fun"and that the big difference was that men can chase down shots much easier and put spin on the ball that female players can't handle. The Williams sisters adjusted their claim to beating men outside the top 350.