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Gogolev withdrew from the 2020 Canadian Championships due to an injury, a bone bruise on his right ankle. He had also experienced a growth spurt. On January 19, 2020 he was selected to represent Canada at the 2020 World Junior Championships. He was also assigned to the 2020 Bavarian Open, where he won the junior men's event by 21 points.

At the 2020 World Junior Championships Gogolev popped his planned triple Axel in the short program into a single, resulting in a score of 67.27 and a placement of 18th. In the free skate he started off strong in the first half of his program, but had some trouble with the jumps in the second half, missing two combinations. He later explained that the tongue of his boot broke as he went to do the planned triple Lutz, inhibiting him from properly performing his remaining jump elements. He placed 14th in the free skate with a score of 124.18 to move up to 17th overall with a final score of 191.45.

Gogolev was named to Skate Canada's 2020-2021 NextGen Team in May.

Gogolev has set five junior world record scores. He holds the Canadian record total score for junior men, as well as the national historical record total scores for pre-novice and novice men. Gogolev is a member of both Skate Canada's National Team and NextGen Team as of the 2019-2020 season.

At the 2019 Canadian Championships Gogolev, skating as a senior, performed a clean short program to take the lead with a score of 88.77 points. In the free skate he popped his quad Lutz but landed a clean quad toe loop as well as a quad Salchow in combination to earn a score of 164.79 points. He took the silver medal with a total score of 253.56 points.

On January 20, 2019 Skate Canada announced that Gogolev was selected to represent Canada at the 2019 World Junior Championships. He skated cleanly in the short program at Junior Worlds, albeit with two jumping passes he described as "a little bit shaky", placing tenth in a closely packed field, only five points behind first-place finisher Pulkinen. In the free program he doubled his planned quad Lutz and fell on a triple Axel but scored 143.66 points, winning a small bronze medal in the free skate and moving up to 5th overall with a score of 220.66 points. He ended his competition season with a performance in the exhibition gala.

On March 14 Gogolev was added as a guest star in the Toronto and Hamilton shows of the 2019 Stars on Ice Canada tour.

In 2019 Gogolev began representing the Granite Club with coach Lee Barkell, while training in Irvine, California under coach Rafael Arutyunyan.

On June 2, 2019 it was announced that Gogolev became a member of Skate Canada's 2019-2020 National Team. He was also included in the list of skaters forming Skate Canada's 2019-2020 NextGen Team posted on July 15, 2019. Gogolev began his season with a win at the 2019 Glacier Falls Summer Classic. He was assigned to compete at 2019 JGP Lake Placid and 2019 JGP Croatia Cup.

Gogolev earned a new personal best short program score in Lake Placid. He came fifth in the free program after taking two falls. Reflecting on his free skate: "I made a mistake on the Axel and it kind of fell apart on the Salchow as well. But I’m happy I was able to get up and do the rest of the program. This program goes through many emotions and that’s what I like about it.” He won the silver medal with a score of 203.70 points.

On the junior level, he is the 2018 Junior Grand Prix Final champion, the 2018 JGP Slovakia champion, the 2019 JGP U.S. silver medalist, the 2020 Bavarian Open champion, and the 2017 Canadian junior national champion.

Gogolev competed exclusively at the senior level this season. He won the inaugural Skate Ontario senior men provincial title. At 2018 Skate Canada Challenge Gogolev ranked seventh in the short program and fourth in the free skate to come fourth overall. He came eleventh in the short program and ninth in the free skate at the 2018 Canadian Championships to end up tenth overall. Gogolev competed with a quad Salchow in his short and free programs this season, and landed a quad toe for the first time in competition. Coach Orser confirmed that he is able to land all the quadruple jumps. He was a member of Skate Canada's NextGen Team this season.

Gogolev was once again chosen to be part of Skate Canada's NextGen Team. In May 2018 he worked with choreographers Marie-France Dubreuil and Samuel Chouinard on an exhibition program for the upcoming season. He was assigned to compete at JGP Bratislava and JGP Canada. At JGP Bratislava Gogolev skated a clean short program to take the lead with a score of 77.67. In the free skate he landed a quad Lutz, quad toe, and quad Salchow triple toe combination to score 148.96 points. He was first in the free skate and won the gold medal with a score of 226.63. Gogolev became the first Canadian skater as well as the youngest skater to land the quad Lutz in competition. In his second JGP event in Richmond, Gogolev was less successful, finishing in fifth place while struggling with his jumps. He was named first alternate to the Junior Grand Prix Final.

On November 4, 2018 Gogolev won another senior provincial title at the 2019 Skate Ontario Sectional Championships. Following the withdrawal of Andrew Torgashev from the Junior Grand Prix Final on November 12, Gogolev was added to the entry list as the sixth competitor. He described himself as "really happy, but not because someone pulled out, but because I was the one going." Gogolev placed second in the short program at the Final, behind Camden Pulkinen. In the free skate, he set a new junior world record score of 154.76 points, taking first place in the free skate to win the gold medal. His score of 233.58 points was also a new junior world record. He is the youngest winner of the men's competition at the Junior Grand Prix Final, breaking a record previously held by Yuzuru Hanyu.

Personal bests highlighted in italic. ISU personal bests highlighted in bold. World records highlighted in bold and italic. (Under the new scoring system, the International Skating Union restarted all records at zero on 1 July 2018. See: "Progression of record scores" under List of highest scores in figure skating.)

Competing at the junior level, Gogolev topped the podium in all events he competed in within Canada. He won the Central Ontario sectional, 2017 Skate Canada Challenge, and the 2017 Canadian Championships junior titles. At Nationals he came from behind to win the title over Conrad Orzel by a margin of four points. In February 2017 he won the advanced novice men title at 2017 Bavarian Open. He attempted a quad Salchow for the first time in international competition at this event, having included it in his free skate this season.

Moving up to the novice level, Gogolev once again had a golden season. He won the Central Ontario sectional, 2016 Skate Canada Challenge, and the 2016 Canadian novice titles. He earned another historical record score at 2016 Challenge. At Nationals, he landed a triple Axel in his free skate and won by over 20 points. After Nationals Coach Orser spoke about Gogolev landing a quad Salchow in practice, and that he had been working on a quad toe loop while being mentored by fellow skater Javier Fernández. In his international debut in March 2016 he won the advanced novice men title at the 2016 Coupe du Printemps.

Competing at the pre-novice level, Gogolev won every competition he entered, including the Central Ontario sectional and Canadian national pre-novice titles as well as the gold medal at the 2015 Canada Winter Games, where he was the youngest competitor. He earned a historical record score while winning the pre-novice title at 2015 Skate Canada Challenge. A video of Gogolev landing a triple Axel at age 10 was shared by his club in January 2015, followed by a video of a landed quad Salchow in May 2015.

Gogolev began skating at the age of six. in 2010. He began skating in Yekaterinburg, ultimately choosing it over skiing. In Russia he learned the triple toe loop, triple Salchow, and double Axel. While competing in Russia he was coached by Alexander Tarasov at DYUSSH No. 8 Lokomotiv. During this time he came to train annually in the summers at The Granite Club.

Stephen Gogolev (born December 22, 2004) is a Canadian figure skater who competes in men's singles. He is the 2019 Canadian national silver medalist.

Gogolev was born on December 22, 2004, in Toronto, Canada to Irina Gogoleva and Igor Gogolev. Gogolev comes from an athletic family. His mother did figure skating and gymnastics, and his father did gymnastics. He has an older brother, Peter Gogolev, a competitive kayaker. Gogolev holds dual Canadian and Russian citizenship.