1. First Final
A year after losing to Agassi, Federer would go on to reach the quarterfinals before Tim Henman stopped his run. In 2000, ranked 34th in the world, the 19-year-old reached his second final of the year after edging out top-tenner Lleyton Hewitt in a third-set tiebreaker. In the final, however, Federer came out on the wrong end of a match going the distance, as the veteran Thomas Enqvist beat him in a roller-coaster five-setter.
2. The Shot
Two years before either of them won a Grand Slam title, young stars Federer and Andy Roddick met in the quarterfinals. Playing a a third-set tiebreak, and trailing 3-1, the big-hitting Roddick saw that serving and volleying—and putting away an overhead—is anything but, as Federer hit what was arguably the greatest shot of his career: