In April 1999, he debuted for the Swiss Davis Cup team against Italy and finished the year ranked world no. 66. During that time, he was the youngest player in the top 100. He also 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. He also made his first appearance at Wimbledon, where he entered as a wildcard. After a five-set match, he lost in the first round to Czech Jiří Novák, who was then ranked no. 59. 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.