January 18th will mark two and a half decades since the tennis icon sealed the first of 369 major match wins and, to mark the occasion, we look back on one of Federer’s landmark career moments.
A junior Wimbledon champion in 1998 and widely recognised as one of the brightest prospects in the game, Federer first attempted to qualify for a Grand Slam main draw at the 1999 Australian Open.
He was beaten by Olivier Delaître in straight sets in the first round of qualifying, though he did not have to wait too much longer to make his Grand Slam debut.
Federer was handed a main draw wildcard into the French Open that summer, pushing third seed and reigning US Open champion Pat Rafter to four sets in an opening-round defeat.
The Swiss was also handed a wildcard into Wimbledon, where he fell in five sets to Jiri Novak, though did not reach the main draw of the US Open – falling in the second round of qualifying to Ivo Heuberger.
Despite disappointment in New York, Federer finished 1999 as the world No 64, having started the season just outside the top 300.
That was more than enough for the 18-year-old to qualify automatically for the Australian Open, and reach the main draw of a major for the first time.
Unseeded in Melbourne, Federer could have drawn top seed Andre Agassi, second seed Yevgeny Kafelnikov, or third seed Pete Sampras – though managed to avoid a seeded player.
However, that does not mean he was handed the easiest draw by any stretch of the imagination.
Federer found himself up against Michael Chang, a former world No 2, the 1989 French Open champion – and an Australian Open runner-up just four years previously.
Chang was not at the peak of his powers at this stage and ultimately Federer outclassed his American rival to win 6-4, 6-4, 7-6(5), and win a Grand Slam match for the first time.
