Though not part of the official 900 ATP matches he played, Federer's victory in the Wimbledon juniors tournament was a harbinger of things to come. It also had some ill effects, burderning Federer with a "can't miss" tag that was tough to shake during his rise through the tennis ranks.
9. Toulouse Open, 1998, first round -- d. Guillaume Raoux, 6-2, 6-2
The first victory for the greatest tennis player of all time came and went with little fanfare. It merited one line in a brief Associated Press recap of the first-round on Sept. 30, 1998: "There was disappointment for French No. 3 Guillaume Raoux, who lost to Swiss qualifier Roger Federer, 6-2, 6-2."
Though Federer had won a small tournament in Brest, France, in 1999, his win on the carpet of Milan was the first big victory of his career. Federer defeated future No. 1 Yevgeny Kafelnikov in the semis and earned $54,000 for the tournament victory.
7. U.S. Open, 2004, quarterfinal -- d. Andre Agassi, 6-3, 2-6, 7-5, 3-6, 6-3
For all his success in New York, Federer hasn't played many memorable matches at the U.S. Open, other than his last two five-set losses at the tournament. During his four-time Open win streak, Federer lost a total of 10 sets (10!). So perhaps his biggest moment came in 2004 when, on his way to his first Open title, the No. 1 seed fended off a challenge from Andre Agassi in five sets. The shot below was the highlight. (Listen to John McEnroe predicting Fed's future greatness. Granted, he had three Slams at the time, but that's still pretty prescient from Johnny Mac.)