In 2014, Chupkov competed at the 2014 European Junior Championships taking 2 bronze medals, in 50 m and 100 m breaststroke and silver in 200 m breaststroke, he won gold with the Russian team in 4 × 100 m medley and 4 × 100 m mixed medley. From 17–22 August, Chupkov competed at the 2014 Youth Olympics in Nanjing, he took five medals including two gold medals in 100 m breaststroke and 4 × 100 m medley relay.