During the height of his career, Mark was known as having one of the fastest services 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 remains the only time that Australia won the Hopman Cup.The honeymoon period with the Australian public, however, did not last.2004 proved a disastrous year in terms of his tennis career and public profile.On 29 March 1999, Philippoussis entered the top 10 for the first time and stayed there for 10 weeks.He advanced to the quarterfinals at Wimbledon in 1999 for the second straight year, where he retired in the second set against Sampras after having won the first set.
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.
Injuries plagued Mark's availability for Davis cup and was the cause of a public rift between team-mates Patrick Rafter and Lleyton Hewitt.
Rafter publicly accused Philippoussis of jerking the team around after he withdrew from a Davis Cup tie in late 2000.
Philippoussis said Rafter was ill-informed and upset by the lack of support and understanding from his team-mates.
Knee surgeries forced Philippoussis out of Davis Cup until February 2003.
Mark suffered a pectoral tear at the end of the second set, which caused him to lose the third and fourth sets.