BONUS: Wimbledon juniors, 1998, final -- d. Irakli Labadze, 6-4, 6-4
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."
8. Milan Open, 2001, final -- d. Julien Boutter, 6-4, 6-7 (7), 6-4
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.)
6. Wimbledon, 2009, final -- d. Andy Roddick, 5-7, 7-6 (6), 7-6 (5), 3-6, 16-14
Federer won nearly 80 percent of points on his serve in this match, so even as he and Roddick were trading games in that epic fifth set, it never felt like Fed was in danger of losing. But what if he had? To lose two epic finals at Wimbledon in a row?
5. French Open, 2003, first round -- l. Luis Horna, 6-7 (6), 2-6, 6-7
Entering the tournament at No. 5 and having won 33 of his last 38 matches, Federer was listless in a straight-set loss to the 88th-ranked Peruivan. Later he would say this match was a turning point in his career. He questioned his motivation and dedicated himself toward his pursuit of greatness. One month later, he would hoist a Grand Slam trophy for the first time.
4. French Open, 2009, semifinal -- d. Juan Martin del Potro, 3-6, 7-6 (2), 2-6, 6-1, 6-4
With Rafael Nadal a surprise fourth-round loser, Federer's path to the career Grand Slam was clear. But then Juan Martin Del Potro got in the way. Federer dropped two of the first three sets in their semi and, for a moment, it looked like his Roland Garros dream would end again. But he broke Del Potro for the first time in the third game of the fourth set and would go on to drop only two more games in the match. The win over Robin Soderling in the final was a mere formality; Federer was 9-0 career against the Swede.
3. Wimbledon, 2008, final -- l. Rafael Nadal, 4-6, 4-6, 7-6 (5), 7-6 (8), 7-9
When casual sports fans remember the classic 1980 Borg-McEnroe Wimbledon final, a fair amount might think McEnroe was the winner of the one-time greatest match ever (probably because McEnroe won that unbelievably 18-16 fourth-set tiebreak). Federer won't get that benefit 20 years from now; everyone will remember that Nadal felled him in their classic '08 final. Though it was the most crushing loss any great tennis player has ever experienced, Federer came back strong. He only dropped three sets en route to the 2008 U.S. Open title.
2. Wimbledon, 2001, fourth round -- d. Pete Sampras 7-6 (7), 5-7, 6-4, 6-7 (2), 7-5
At 19, Federer stunned Pete Sampras on Centre Court, snapping the American's 31-match winning streak on the grass of Wimbledon. Pistol Pete had entered the match having won 56 of his last 57 matches at the tournament. (Interesting note: Federer earned the name "Yankee Killer" after that match since he had won seven straight times against American players. He would run that total to eight before Andre Agassi beat him in the fourth round at the U.S. Open later that year.) Though he would lose in the next round to hometown favorite Tim Henman, Federer's win over Sampras put the tennis world on notice. It would take two years for him to live up to those expectations.
1. Wimbledon, 2003, final -- d. Mark Philippoussis, 7-6 (5), 6-2, 7-6 (3)
The one that started it all. Federer had never advanced past the quarterfinal at a Grand Slam before cruising to a win at Wimbledon in 2003. He dropped one set through the fortnight and hit only nine unforced errors in the final. After the match he wondered about his future. "To win Wimbledon as a first Grand Slam," he said, "I hope it's not going to be my last."