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.

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.
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.
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.
Stephen Gogolev