He helped the Dragons to the Central League Title in 1999, but would lose in the Japan Series in 5 games to the Fukuoka Daiei Hawks.

In 2004, Kawakami went 17–7 and led Chunichi to the Central League Title, though they fell to the Seibu Lions in 7 games in the Japan Series.

That year, Kawakami was named Central League MVP and received the Eiji Sawamura Award as Japan's best pitcher.

In 2007, Kawakami helped the Dragons end a streak of 53 years without a championship as they beat the Nippon Ham Fighters in 5 games.

[7] After spending the entirety of the 2011 season pitching at the AA level for the Mississippi Braves, Kawakami agreed to a contract with his previous team, the Chunichi Dragons of Japan's Central League.

[12] Kawakami throws a fastball around 90 mph (tops out at 94), shuuto (sinker), slow curveball, splitter, and a good cutter.