Roger Federer's first ATP Tour-level tournament was the 1998 Gstaad Open, where he faced Lucas Arnold Ker in the round of 32 and lost, 4–6, 4–6.
In July 1998, the 16-year-old Federer played his first ATP Tour event, the Swiss Open Gstaad, in his home country of Switzerland, losing to No.
[5] In February 1999, Federer reached the quarterfinal of ATP tournaments in Marseille and Rotterdam, defeating the reigning champion of the 1998 French Open, Carlos Moyá, in the former, to enter the Top 150 before the Miami Masters.
[6] His rise through the rankings was noticed by the Swiss Davis Cup captain Claudio Mezzadri, who invited him to join the squad for the World Group first round clash against Italy on home soil in Neuchatel.
[7] He then competed in his first Grand Slam tournament at the French Open, but lost to Patrick Rafter in the first round after a four-set match.
[9] In the same tournament, Federer partnered Lleyton Hewitt in doubles, where they reached the round of 16, losing to Rafter and Jonas Björkman in another five-set match.
[10] Despite losing in the first rounds of both the French Open and Wimbledon and having just turned 18, he entered the world's Top 100 for the first time on 20 September 1999.
[12] Later that month, Federer won his first and only singles ATP Challenger title in Brest, defeating Max Mirnyi in the final.
"[18] In February 2001, Federer won his first ATP tournament after defeating Julien Boutter in the final of the Milan Indoor.
[12][19] During the same month, he won three matches for his country in its 3–2 Davis Cup victory over the United States in front of a home crowd in Basel, thus becoming only the fifth man in history to win every match against the United States, the most successful country in Davis Cup history with 31 titles.
[12] After a match against Marat Safin at the Rome Masters, in which both players threw their racquets several times, Federer decided to change his temper after watching himself in the highlight reel.
[21] His international breakthrough came at the Wimbledon Championships, when the 19-year-old Federer and the four-time defending champion and all-time Grand Slam leader Pete Sampras walked onto Centre Court for their only meeting in the fourth round.
After early-round exits at the French Open and Wimbledon, Federer suffered the devastating loss of his long-time Australian coach and mentor, Peter Carter, in a car crash in August.
In the third round, which he and Ferreira lost to Joshua Eagle and Sandon Stolle, Federer played the match wearing a black armband in honor of Carter.
[27] Although he suffered first-round losses in the three tournaments he entered after Carter's death, Federer gathered himself together and began playing with more determination than ever.
This qualified him for the first time for the year-end Tennis Masters Cup, where he won all of his matches in the round-robin stage with the loss of only one set before losing the semifinals to the then-world no.