Andy Roddick and Roger Federer's careers largely overlapped. They played many matches against each other, resulting in Roddick losing multiple times at Wimbledon.
Despite the competitive history, the two developed a professional relationship characterized by mutual respect. Nonetheless, Roddick often found the Swiss to be a challenging opponent.
However, in a recent episode of his "Served with Andy Roddick" podcast, the American former player discussed an instance from many years ago where he expressed frustration with a line of questioning from the media that he deemed disrespectful to not only Federer but other players as well:
"Another time I got salty, I remember, I was playing Roger somewhere. It might have been Miami. He was ranked three in the world, and I was ranked around 30. Someone asked, "He’s ranked three in the world, he’s really slipping, isn't he?" They were asking in a way that I'm digesting like, 'Is Roger a bad player now?'" [20:07]
Roddick instructed everyone present to participate in a demonstration to express his displeasure with the line of questioning:
"'Everyone in here, raise your hand. Exactly three of you are top three in the room, and exactly all of you would tell me that you're good at your job.' It was like silence. (...) This line of questioning is frankly offensive to anybody who is not him also. I would kill for his worst year. Are we kidding ourselves?"
Roddick emphasized that in tennis, somebody who is 30th in the world is widely successful among the thousands of professional players, but that might pale compared to some of the best in the world.
Andy Roddick bested Roger Federer three times

Andy Roddick managed only three wins in the 24 times he played against Roger Federer. He first came close at the Basel event in 2001, but Federer bested him in three sets.
Roddick's first win came two years later at the Masters event in Montreal, Canada, the fifth time the two played against each other. Roddick then lost 11 matches consecutively before beating his rival in Miami in 2008. He then lost a couple more before besting him in what ended up being the final match they played. That was in Miami again in 2012.
Roddick would retire that year, ending a Hall of Fame career.
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