Career
In his early career, Chupkov started swimming to improve his health. He is coached by Aleksandr Nemtyrev and trains at the Sports School of Olympic Reserve "Youth of Moscow" for swimming. Chupkov swam distances of 100 m and 200 m breaststroke in 2014.
In 2013, Chupkov competed at the 2013 European Youth Summer Olympic Festival taking gold medal in 200 m breaststroke and silver in 100 m breaststroke.
In August 17–22, Chupkov competed at the 2014 Youth Olympics in Nanjing, he took 5 medals including two gold medals in 100 m breaststroke and 4×100 m medley. He also competed in the 50 and 100 meters breaststroke. and 4x100 m mixed medley (with Daniil Pakhomov, Arina Openysheva and Maria Kameneva at a time of 3:4953).
Chupkov broke two junior world records including shattering a previous record held by himself set at the 2014 Youth Olympics. He was chosen as the flag bearer representing the Russian Federation at the closing ceremony of the Games.
In August 2-9, Chupkov appeared in his first senior Worlds at the 2015 World Championships in Kazan, he qualified in men"s 200 m breaststroke finals finishing in 7th place in a time of 2:09.96, after previously setting a junior world record in the semifinals heat in a time of 2:09.64.
In August 25-30, Chupkov then competed at the 2015 World Junior Championships in Singapore, he took individual medals winning gold in men"s 100 m breaststroke (1:0019) and in 200 m breaststroke (2:1019, a meet record), but only finished 7th in men"s 50 m breaststroke finals. In relay events, Chupkov also competed in 4x100 m mixed medley (with Daniil Pakhomov, Irina Pridhoko and Arina Openysheva) were Russia threw in a new Junior World record touching in at 3:45.85 and in men"s 4x100 medley (with Daniil Pakhomov, Vladislav Kozlov, Roman Larin, touching in 3:3644), taking the meet record.