Kirillow started in Krasnogorsk for the first time in the Eastern Europe Cup in December 2013 and finished 151st place over 15 km classic. At the Nordic Junior World Ski Championships in 2016 in Râșnov , he won the silver medal with the relay. He also achieved 37th place over 10 km classic and sixth place over 15 km freestyle. In March 2016 he became the Russian junior sprint champion in Izhevsk . In the 2016/17 season he achieved six top ten placements, including second place in Krasnogorsk over 15 km classic, eighth place in the overall ranking of the Eastern Europe Cup. At the U23 World Ski Championships 2017 in Soldier Hollow , he came in 16th place in the sprint. In January 2018 he ran his first World Cup race in Planica . He got his first World Cup points with the 28th place in the sprint. At the U23 World Ski Championships in Goms in January 2018 , he ran to 32nd place in the sprint, 16th place over 15 km classic and ninth place in the skiathlon . The following year he won the silver medal in the 30km mass start race at the U23 World Ski Championships in Lahti . At the Winter Universiade 2019 in Krasnoyarsk , he won the classic bronze medal and the pursuit over 10 km and the gold medal with the relay. In the 2019/20 season he took third, second and first place, fourth place in the overall ranking of the Eastern Europe Cup.