In the spring of 2020, Chupkov signed for the Toronto Titans, the first Canadian based professional swim team in the ISL, in their inaugural season.

In the Autumn of 2019 he was member of the inaugural International Swimming League swimming for the Energy Standard International Swim Club, who won the team title in Las Vegas, Nevada, in December. He won the 200m breaststroke at both the Indianapolis and London matches.

On 20 April 2015, at age 18, Chupkov won the gold medal and became the Russian champion in the 200 m breaststroke. He also competed in the 50 and 100 meters breaststroke.

In June 2015 at the inaugural 2015 European Games in Baku, Chupkov won four gold medals, in 200 m breaststroke, 100 m breaststroke, 4 × 100 m medley (with Daniil Pakhomov, Vladislav Kozlov and Filipp Shopin touching in 3:36.38), a new junior world record breaking the previous record held by Russia in 3:38.02 at the 2014 Youth Olympics. and 4 × 100 m mixed medley (with Daniil Pakhomov, Arina Openysheva and Maria Kameneva at a time of 3:49.53). 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.

Chupkov appeared in his first senior Worlds at the 2015 World Championships in Kazan, where he qualified in the 200 m breaststroke final finishing in 7th place in a time of 2:09.96, after previously setting a junior world record in the semifinals in a time of 2:09.64.

Chupkov also competed at the 2015 World Junior Championships in Singapore; he took individual medals winning gold in the 100 m breaststroke (1:00.19) and the 200 m breaststroke (2:10.19, a meet record), but finished 7th in the 50 m breaststroke final. In relay events, Chupkov competed in 4 × 100 m mixed medley (with Daniil Pakhomov, Irina Pridhoko and Arina Openysheva) where Russia set a new Junior World record touching at 3:45.85, and in the men’s 4×100 medley (with Daniil Pakhomov, Vladislav Kozlov, Roman Larin, finishing in 3:36.44), taking the meet record.

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.

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. He has been member of the Russian Federation youth national team in swimming since 2013. 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 the gold medal in 200 m breaststroke and the silver medal in the 100 m breaststroke.

Anton Mikhailovich Chupkov (Russian: Антон Михайлович Чупков ; born 22 February 1997) is a Russian competitive swimmer.