On February 10, 1999, following the 1998–99 NBA lockout, Allen signed a six-year, $70.9 million extension with the Bucks, making him the highest paid player in franchise history at that point. The 1998–99 season saw Allen make his first playoff appearance, with the Bucks earning the seventh seed. There they were swept by the Indiana Pacers in the first round despite Allen averaging 22.3 points per game. The following season, on January 20, 2000, Allen recorded a career-high 13 assists in a loss to the Seattle SuperSonics. A month later, Allen played in his first All-Star Game, where he had 14 points in 17 minutes. During the 1999–2000 season, Allen led the Bucks in scoring during the regular and post-season.