Dupree went undrafted in 2003, but signed during the 2003–04 season with the Chicago Bulls. After his rookie season, he signed a contract with the Detroit Pistons, but was infrequently used by coach Larry Brown. Dupree was traded to the Minnesota Timberwolves prior to the 2005–06 season for a second-round draft pick. He re-signed with the Pistons on July 17, 2006. On December 14, 2007, he was waived so the Pistons could make room for other players obtained in a trade with the Charlotte Bobcats. He was signed to a ten-day contract by the Seattle SuperSonics on April 3, 2008, becoming the last player to sign with the Sonics.