Over two seasons (2018-20) with HK Hradec Kralove, Chalupa tallied 38 points (11G, 27A) in 98 games and skated in six playoff contests. During the 2017-18 season, he made appearances with HC Plzen of the Czech Republic League, HC Stadion Litomerice of the Czech Republic-2 League, HC Slovan Usti nad Labem of Czech Republic-2 League, HC Klatovy of the Czech Republic-3 League and HC Plzen U20 of the Czech Republic U20 League totaling 16 goals and nine assists across 57 games.