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Roger starts working with the Swedish coach Peter Lundgren. The Olympic Games in Sydney are a great success; he reaches the semi-finals in a strong field. He meets the Swiss tennis player, Mirka Vavrinec, in the Olympic village and from the last day on, they are a couple.  

Roger survives the first two rounds at the Australian Open, making his best Grand Slam appearance so far. Thereafter he reaches his first ATP finals in Marseilles, which he loses to his Davis Cup colleague Marc Rosset. On March 6th, he has already reached his goal for the year of being ranked in the top 50 when he is ranked 49th.

Roger leaves Swiss Tennis in April to stand on his own feet. In the course of this change, he decides upon Peter Lundgren as his private coach. The long-haired Swede will assist him until end-2003 and lead him to his first Grand Slam title in London.  

The clay season passes badly for Roger; he loses in the first rounds several times. Only at the French Open does he win matches on clay and reaches the round of 16. However, he again loses in the starting round at Wimbledon and also in the third round at the US Open.

The Sydney Olympics are a highlight for the 19-year old Roger. The size of the event, the athletes from various countries and disciplines as well as the Olympic spirit in the Olympic village fascinate him. Despite strong competitors, he reaches the semi-finals, which he loses to the German Tommy Haas. His defeat in the match for the 3rd place against the lower ranked Frenchman Arnaud de Pasquale is particularly hard to bear. Nevertheless, the tournament must be seen as a success, despite the disappointment.

Even though Roger leaves without a medal, he does not leave Sydney empty-handed. He meets the Swiss tennis player, Mirka Vavrinec, in the Olympic village and falls in love with her. He kisses his future wife and mother of his children on the last day of the Olympic Games. The love birds manage to keep their relationship a secret from the public until the summer of 2001.

Roger reaches his second finals on the ATP circuit in October; his first in the tournament in Basel – his hometown – but loses to the Swede Thomas Enqvist. The year does not end all too well for him; he only manages to win three more matches. He narrowly misses his season goal of reaching the top 25, by being ranked 29th.

The appointment of Pierre Paganini as his fitness coach in December further completes his team.