On October 11, 2018, during the third Pittsburgh game of the 2018–19 season, Kessel scored his sixth career hat-trick, which occurred as his first natural, and first as a Penguin. From February 1 to March 5, 2019, Kessel did not score a goal in 16 games (however, he collected 11 assists), which was the longest goal-drought in his entire career. On March 19, 2019, Kessel played in his 320th consecutive game for the Penguins, passing Craig Adams for the longest in their history. After the last game of the regular season, Kessel was second in points for Penguins, and led the league with 10 game-winning goals.