Fed's most painful losses? Fed would probably say, all his losses to Berdych. I believe Federer truly hates Berdych. You see that look of disgust in his eyes everytime he plays Berdych. I don't think Federer minds losing to Rafa, he recognizes him as a great player. Everytime he loses to Nadal, he looks like he's just happy and contend to be on the court with him.