Under the management of Dennis Holmberg, the Doubledays won the Pinckney Division title for six straight years in 2002, 2003, 2004, 2005, 2006, and 2007, but failed to win the league championship for the first five of those years. After losing in the first round of the playoffs for the first three years of their streak, they advanced to the New York–Penn League championship series before being swept by the Staten Island Yankees. In 2003, the Doubledays led all of baseball in winning percentage (.757).