At ages 13 and 14, Kournikova made headlines in international junior tennis, winning several tournaments including the 1995 Italian Open. She was 14 years old when she ended 1995 as Junior European Champion Under 18 and ITF Junior World Champion Under 18.

Kournikova debuted in professional tennis at age 14 in the Fed Cup for Russia, the youngest player ever to participate and win. At age 15, she reached the fourth round of the 1996 U.S. Open, only to be stopped by then-top ranked player, Steffi Graf. Kournikova was a member of the Russian delegation to the 1996 Olympic Games in Atlanta, Georgia. In 1997, as a 16-year-old, she reached the semi-finals of Wimbledon, where she lost to the eventual champion, Martina Hingis by a score of 6–3, 6–2.

1998 was her breakthrough year, when she broke into the WTA's top 20 rankings for the first time and scored impressive victories over Martina Hingis, Lindsay Davenport, and Steffi Graf. Kournikova's two Grand Slam doubles title