Medvedev was one of the best players in the junior division, winning the French Open in his last junior year in 1991 . Shortly thereafter, he switched to the ATP Tour and was immediately successful there. As a 17-year-old he won the tournaments in Genoa and the Mercedes Cup in Stuttgart in 1992 . With his solid baseline game , he was one of the world's best players, especially on clay.
After tournament victories in Monaco and Hamburg , Medvedev achieved his best position in the individual world rankings in May 1994 with position 4 .
Medvedev won his last tournament victory in 1997 in Hamburg . After that he was barely able to achieve any success. In 1999 he won, only in 100th place in the world rankings, among others against Pete Sampras and Gustavo Kuerten and reached the final of the French Open . There he was defeated by Andre Agassi despite a 2-0 lead . It was Medvedev's last participation in the final on the tour. In 2001 he ended his career.
He won a total of eleven titles in his career, three of them at the German Open at Hamburg's Rothenbaum (1994, 1995, 1997).
Medvedev was in a relationship with the German tennis player Anke Huber for a while. His older sister Natalija Medvedeva was also a professional tennis player.