Roddick shook off a sluggish start against the unseeded Benneteau to set up a quarterfinal clash with Federer.
The American takes a 1-15 lifetime record into his match against Federer, his only win coming in 2003 in a third set tie-break in the Rogers Masters semifinals.
Roddick said, "He's one of the few guys that I've probably played three or four really, really good matches against him and came up short. I think I have brought out the best in him a couple of times."