Medvedev, an alumnus of CSKA Moscow youth school, started his professional career in 1995 playing for Orekhovo in the Russian Second Division.

Following this achievement, Medvedev signed for the Russian Premier League club FC Saturn Ramenskoye in 1999.

Two years later, Medvedev moved to the Russian First Division club Sibir Novosibirsk.

With Sibir Medvedev, as the team's captain, became the First Division top scorer, best striker and best player in 2009, and helped the club to be promoted to the Russian Premier League for the first time in its history.

On 21 April 2010, Medvedev's hat-trick led the team to the 2009–10 Russian Cup final, and to the European stage.