Some of the most squirm-worthy moments in dating awkwardness are often seen on reality shows. Not usually, but that sure doesn't mean we won't watch them try and try again!Be sure to vote for your favorite dating reality shows and vote down the dating shows you absolutely can't stand.He appeared in his second Olympic Games in Sydney, losing in the third round to eventual gold medalist Yevgeny Kafelnikov.Philippoussis finished 2002 in the top 100 (seventh time in eight years), despite not winning a title.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.During that match, Philippoussis suffered a moderate cartilage tear in his left knee and underwent arthroscopic surgery four days later.
He reached a career-high singles ranking of World No. He has had a minor career in modelling and starred in the American reality television dating show Age of Love.
On 29 March 1999, Philippoussis entered the top 10 for the first time and stayed there for 10 weeks.
He advanced to the quarter-finals at Wimbledon in 1999 for the second straight year, where he retired in the second set against Sampras after having won the first set.
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 World No. He reached the fourth round at the Australian Open, losing to eventual champion Andre Agassi. 2, 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.