He defeated Pete Sampras in the quarterfinals in three tight sets, before losing to Boris Becker in the semifinals.

At that year's French Open, he reached the semifinals, falling in four sets to two time former champion Sergi Bruguera.

Then, he surprised many by winning the US Open, defeating Andriy Medvedev, Magnus Norman, Lionel Roux, Andre Agassi, Magnus Larsson, and Michael Chang before beating Greg Rusedski in a four-set final; he was the first non-American to win the title since Stefan Edberg in 1992.

This was his first Grand Slam title, and catapulted him ahead of Chang to finish the year ranked #2 in the world (behind only Pete Sampras).

He added that a tennis player must come back and win a Grand Slam again in order to be considered great.

[3] Entering the U.S. Open as the defending champion, Rafter reached the final by defeating Hicham Arazi, Hernán Gumy, David Nainkin, Goran Ivanišević and Jonas Björkman before besting Sampras in a five-set semifinal.

[4] Rafter then defended his US Open title by defeating fellow Australian Mark Philippoussis in four sets, committing only five unforced errors throughout the match.

Rafter won the Australian Open men's doubles title in 1999 (partnering Jonas Björkman), making him one of few players in the modern era to win both a singles and doubles Grand Slam title during their career (fellow countryman Lleyton Hewitt would later achieve this feat in 2001).

[7] As the two-time defending US Open champion, Rafter lost in the first round of the tournament, retiring in the fifth set against Cédric Pioline after succumbing to shoulder tendinitis.

Rafter faced Sampras in the final, who was gunning for a record-breaking seventh Wimbledon title overall (and seven in the past eight years).

Rafter played on the Australian Davis Cup Team that lost in the final in 2000 (to Spain) and 2001 (to France).

Much like the previous year's semifinal, this match also received praise for the quality of play that the two men displayed.

He played his last match at the Davis Cup final on rubber, winning the singles but losing the doubles.

In January 2003, he announced his retirement from professional tennis, stating that he had lost all motivation to compete at the top level.

[16] Rafter did return at the beginning of the 2004 season to play doubles at two tournaments only; the 2004 Australian Open and the 2004 AAPT Championships (in Adelaide).

The comeback, however, was short-lived, as the pair went down in straight sets to eventual runner-ups Eric Butorac and Raven Klaasen in the first round.

[21] At the 2009 AEGON Masters Tennis, Rafter lost his opening round robin match against the 1987 Wimbledon Champion and fellow Aussie Pat Cash 2–6, 6–2, 10–6.