While Roger Federer may be behind in the “greatest of all time” debate by the numbers, when it comes to technique alone, he is preferred by many of his peers. It has often been said that nobody was more elegant, fluid, or effective than him. But what was his most difficult shot? Former World No. 1 Andy Roddick, one of his early big rivals, has revealed which aspects of Federer’s game he struggled with the most.

Speaking to Tennis Channel in 2020, Roddick said that his ability to “with very, very small movements, put the ball back in play. Once we were neutral, it was to his advantage,” explaining that “His ability to counter my pace with very little movement and make a ton of returns was frustrating.”

Apart from Federer’s physical control, Roddick also said that his serve was one of the most difficult to read. “I mean this in a positive way because I think the person who messed with their toss and pacing of their serve, who could play that kind of hurry-up, was Agassi. He wasn’t an unbelievable server in terms of pace and movement, but he pitched such a good ballgame. Andre was almost like Greg Maddux, whereas Pete [Sampras] was more powerful and had the placement. I think Roger was almost a hybrid between the two,” he explained.

He compared Federer’s serve with the great pitchers. “The greatest pitchers aren’t scared to throw a curveball on a 3-2 count—Roger was the same way. He would throw a 97 mph kicker for a first serve just as easily as he would hit the big one out wide. He didn’t really have predictable habits, which made it frustrating,” Roddick explained.

Andy Roddick and Roger Federer during the 2005 Wimbledon final (Clive Brunskill/Getty Images)

He continued, He could move the second serve around the box, shorten it, lengthen it, and hit it both ways. What he didn’t have was just natural pace—he still hit a great serve, 125, 126 consistently, which, if you’re hitting your spots, is plenty. He was a great pitcher in terms of keeping you on edge, never letting you know what was coming—fast, slow, with no obvious tendencies. It was annoying.”

Roddick and Federer’s head to head

Andy Roddick and Roger Federer faced each other 24 times on the ATP Tour, with Federer dominating their head-to-head record 21-3. Their rivalry was defined by several major finals, with Federer consistently getting the upper hand in Grand Slam title matches. Roddick’s three victories came in lower-stakes tournaments, including the 2003 Canada Masters and 2008 Miami Open.

The most significant meetings between the two came in Grand Slam finals, particularly at Wimbledon, where they clashed in the championship match three times. Federer defeated Roddick in the 2004, 2005, and 2009 Wimbledon finals, with their final encounter being the most memorable. In 2009, Roddick played one of the best matches of his career, holding serve for most of the five-set battle before Federer broke him for the first time late in the final set, winning 16-14.