Kessel scored the first Bruins goal of the 2008–09 season, in a 5–4 Bruins victory against the Colorado Avalanche. Kessel ended the regular season on a high note, scoring his second career hat-trick in the April 12, 2009, 6–2 visitors' victory against the New York Islanders, and amassing the highest number of NHL regular season goals so far in his career with 36, the most on the Bruins that season. He also tied Ed Olczyk for longest point streak by an American-born NHL player (18 games, 14 goals and 14 assists for 28 points during streak) in late 2008. It is now the third-longest such point streak after Patrick Kane's 26-game streak in late 2015 and 20-game streak in the beginning of 2019.