Milwaukee has a rich and storied history with its gay softball. In 1977, four teams arranged "pick-up" games to play softball during summertime. Each week these teams would compete against one another at the Mitchell Park Domes fields with the loser of each game buying the winning team a half barrel of beer at their home bar and thus the Saturday Softball Beer League was created. Milwaukee's inaugural tournament, the WRECKROOM CLASSIC was held over Memorial Day Weekend in 1978. Milwaukee, along with San Francisco, New York City, Los Angeles and Toronto formed NAGAAA. NAGAAA awarded Milwaukee the host city for the 1979 Gay Softball World Series. Teams from Boston, Chicago, and the Twin Cities were invited to participate along with the founding cities. That year, the Los Angeles Rusty Nails took the GSWS title.

In 1985, Milwaukee again hosted the Gay Softball World Series as we "Captured the Spirit". Milwaukee was also host to the first city Women's Division in a GSWS. That year, the Houston Briarpatch "captured their spirit" with a first place finish in the Open Division while the San Diego Spoilers won the Women's Division. The highlight of this GSWS were the parachutists landing on the infield next to the Steinway Piano while the National Anthem's of Canada and the United States played.

1986 brought major change to SSBL and the Classic. SSBL changed the name from the Wreckroom Classic to the Milwaukee Classic. That year, was the beginning of a stretch of 15 years of the Milwaukee Classic ending in 2001.

In 2002, big changes again, occurred with SSBL. The Classic changed names once again, with the tournament changing not only the name but also the weekend of the tournament. The Dairyland Classic tournament over Labor Day Weekend was born. Its first year saw 14 teams enter into the tournament in 2002.

Also in the off-season in 2002, the Milwaukee Kosmos were born. The Milwaukee Kosmos are a traveling team that goes to other out-of-town tournaments. They are sponsored by many of the local bars. The purpose of the Milwaukee Kosmos is to promote to the nation the Dairyland Classic in hopes that different teams will come to Milwaukee's tournament and also to show other major cities that Milwaukee softball is alive and well.

In 2004, SSBL expanded back to 10 teams in its league while adding a team, once again, from Madison, Wisconsin. Games were held at Mitchell Field from 11:00 to 5:00. Food and Beer (SSBL's trademark) are always available at the park. The Dairyland Classic had 22 teams this year.

The biggest change in SSBL came when SSBL approached Miller Park and the Milwaukee Brewers. This was the start of a great partnership which still exists today. Come out on most home dates to Miller Park and behind home plate you will see a hard working group from SSBL selling concessions at one of the largest stands in ballpark. To date, the league has raised over $150,000. In 2006, SSBL expanded once again and in a big way. A second division was added to support our sister city, Madison, Wisconsin. The cities play against each other twice a year, much in the same way that the American and National Leagues play each other in MLB.

The biggest tournament that Milwaukee has ever held to date occurred Labor Day weekend in 2007 where 57 teams participated in Dairyland Classic XXX. The highlights of the tournament were the Klements racing sausages guest appearance along with the mayor of Milwaukee, Tom Barrett.