In relay events, Chupkov competed in the 4×100 metre mixed medley (with Daniil Pakhomov, Irina Pridhoko and Arina Openysheva), where Russia set a new world junior record at 3:45.85, and in the 4×100 metre medley (with Daniil Pakhomov, Vladislav Kozlov, Roman Larin, finishing in 3:36.44), setting a new championships record.

[5] In June 2016 as part of the Mare Nostrum stop in Canet-en-Roussillon, France, Chupkov broke the Russian record of 2:08.62 set in 2013 by Vyacheslav Sinkevich in the 200 metre breaststroke with a time of 2:08.53.

[9][10] For the stop of the 2017 Mare Nostrum held in Barcelona, Spain, Chupkov set a new Russian record in the long course 100 metre breaststroke with a time of 59.39 seconds on 13 June.

[16] In the final of the 200 metre breaststroke the next day, 28 July, Chupkov won the gold medal in a time of 2:06.96, lowering the previous Championships, European, and Russian records he had set in the semifinals and finishing over three-tenths of a second ahead of silver medalist Yasuhiro Koseki of Japan and over half a second ahead of bronze medalist Ippei Watanabe of Japan.

[20] In the 200 metre breaststroke, Chupkov won the gold medal with a time of 2:06.80 and set new Championships, European, and Russian records in the event.

[23] In the prelims heats of the 200 metre breaststroke, he qualified for the semifinals ranking second behind first-ranked Matthew Wilson of Australia and ahead of third-ranked Marco Koch of Germany with a time of 2:08.22.

[33] Chupkov also won the gold medal in the 200 metre breaststroke, finishing in 2:07.95 and over half a second ahead of the silver medalist in the event, Qin Haiyang of China.

[34][35] On the breaststroke leg of the 4×100 metre medley relay, Chupkov split a 58.72 to help win the silver medal in a final time of 3:33.57.

[34] At the 2019 FINA Swimming World Cup stop in Kazan in November and conducted in long course metres, Chupkov broke the Russian record of 59.05 set by Kirill Prigoda in the 100 metre breaststroke with a time of 58.94 seconds and won the gold medal in the event, finishing four-hundredths of a second ahead of silver medalist Arno Kamminga of the Netherlands.

[38][39][40] At the 2020 European Aquatics Championships held in Budapest, Hungary in May 2021, Chupkov placed tenth in the semifinals of the 100 metre breaststroke on 17 May with a time of 59.49 seconds.

[41] In the 200 metre breaststroke final on 20 May, Chupkov won the gold medal with a time of 2:06.99, which made him the only medalist to swim the race in less than 2:07.00.

[51] Ranked across all four stops of the World Cup circuit for his performances, Chupkov came in at number 22 overall amongst all male competitors in terms of total number of points scored and ranked as the second-highest scoring male competitor representing Russia behind Vladimir Morozov.