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Philippoussis returned to professional tennis seven weeks later at the Indianapolis Tennis Championships and lost his second round match after receiving a bye in the first round. 2000 was the fourth consecutive year in which Philippoussis finished in the top 20, at No. He reached the fourth round at the Australian Open, losing to eventual champion Andre Agassi. 2 Sampras 8–6 in the fifth set at the French Open in a first-round match, but lost in the fourth round to Juan Carlos Ferrero.
He did not play again until October in Singapore, where he lost in the second round. For the third consecutive year, he made it to the quarterfinals at Wimbledon, losing again to Agassi.
It seemed to work, as he made the 2003 Wimbledon final, finally losing to Roger Federer, 6–7(5), 2–6, 6–7(3).
During a 2003 Wimbledon tennis match against Andre Agassi (6–3, 2–6, 6–7 (4–7), 6–3, 6–4), he set a new Australian tennis record of 46 aces served in a match, three aces short of the overall ATP Tour record then held by Richard Krajicek.
During the height of his career, Philippoussis was known as having one of the fastest serves in the game. In January 1999, Philippoussis and Jelena Dokić won the Hopman Cup for Australia, defeating Sweden's Åsa Carlsson and Jonas Björkman in the final tie.
This was the first time that Australia won the Hopman Cup and the only time, until Nick Kyrgios and Daria Gavrilova won in January 2016.
Philippoussis suffered a pectoral tear at the end of the second set, which caused him to lose the third and fourth sets.
Sampras later remarked that he "dodged a bullet out there".
By then, Pat Rafter had retired, and John Fitzgerald and Wally Masur were the new Davis Cup captain and coach.
The impact of these changes was instantly recognised, as team harmony was at its highest throughout the year.
In 1996, he reached the 4th round of the Australian Open upsetting Pete Sampras in the 3rd round and in doubles with Patrick Rafter.
On , he recorded a personal best 229.0 km/h (142.3 mph) serve in a game he lost to Albert Costa. Open, Philippoussis reached his first Grand Slam final, losing to fellow Australian Patrick Rafter.