Defenseman Milan Chalupa was Detroit's third-round pick, 49th overall in the 1984 NHL Entry Draft. Chalupa was a teen star in his native Czech Republic and joined the elite Jiskra Havlickuv junior team at the age of just 13 in 1966. He remained with the club for six years, developing into a strong defensive star. Throughout the mid 1970s and early 1980s Chalupa played for Dukla Jihlava for eleven years. He was also a member of the 1976 and 1980 Czech Olympic teams and participated in seven games for the national team in the 1976 and 1981 Canada Cup tournaments.
Chalupa played his entire 14-game NHL career in a Red Wings uniform in 1984-85, scoring five assists. He also appeared in one game with the Red Wings' farm team in Adirondack.
From 1985 through 1991, Chalupa played with EHC Freiburg in the German Elite League before going into a two-year retirement. However, Chalupa missed playing hockey at the elite level and decided to return for one final season with Dukla Jihlava. In 12 games, he picked up four assists before retiring from pro hockey at the age of 40.