Roger Federer's early career

Roger Federer's first ATP Tour-level tournament was the 1998 Gstaad Open, where he faced Lucas Arnold Ker in the round of 32 and lost, 4–6, 4–6. Federer's first final came at the 2000 Marseille Open, where he lost to fellow Swiss Marc Rosset, 6–2, 3–6, 6–7. Federer's first tournament win was at the 2001 Milan Indoor, where he defeated Julien Boutter, 6–4, 6–7, 6–4. The most prestigious finals he contested at this time included the 2002 Miami Masters, where he lost to Andre Agassi, 3–6, 3–6, 6–3, 4–6. Shortly thereafter, Federer won his first Masters Series event at the Hamburg Masters on clay, 6–1, 6–3, 6–4, over Marat Safin.

Federer made ten singles finals between 1998 and 2002, of which he won four and lost six. Federer made six doubles finals during this time, but lost the most prestigious of them at the 2002 Indian Wells Masters. The most prestigious events he won were the Hamburg Masters in 2002 and two Rotterdam 500 series events in 2001 and 2002.