During 2006, the league grew to eight teams with the addition of Black and Maroon. We began playing our first interleague games with Milwaukee and had a competitive league in the fall that consisted of four teams. At the end of the season, we said good-bye to Doug Hinderliter and his partner Troy Kimble as they moved to the Twin Cities area. We will always be grateful for their hard work and dedication in creating this league. At the end of the season, we created the Doug Hinderliter Character Award to honor a player each year who shows exemplary character both on and off the field.

The summer of 2004 was when Madison Gay Softball was introduced. Doug Hinderliter, "the founder of Madison Gay Softball" and later the league's first commissioner, started this league out of his desire to provide the Madison Gay Community with an opportunity to participate in, and grow an appreciation for, the game of softball. We started with six teams: Blue, Green, Orange, Red, Violet, and Yellow.