The league was founded in 1991 by Steven Zajac (Austin Outlaws), Yaro Zajac (Vancouver Iron Fist), Michael Matiash (Arkansas Falcons), Brian Dissler (Columbia Crusaders), Paul Barbosa (Newark Crimewave) and Eugene Mullin (Maine Lobsters). The first draft was held in March of 1991. The software used at the time was MicroLeague Baseball II. The first season consisted of 150 games. Cecil Fielder was selected as the first overall pick. He would end up getting traded to Arkansas. Vancouver won the World Series, naming Bud Black, series MVP. Eugene relinquished his team to Ryan DeRonde near the end of the season. Ryan changed his team name to the San Antonio Gun Slingers.

In 1992, the season was expanded to 162 games and the league expanded for the first time. Brent Campbell (Louisiana Lightning) added the Scranton Sparrows to the league. The Newark Crimewave became the Tampa Bay Sweat Sox. Juan Guzman was selected with the first overall pick.

In 1993, the league expanded by three teams -- the Cheyenne Warhawks, the Charleston Chiefs, and the Waikiki Keys. The Slingers were also taken over by Daryl Melillo and renamed the Sacramento Seahawks. The Warhawks went on to the playoffs, while the Keys set single season records for most strikeouts as well as worst regular season record. Cheyenne's Deion Sanders was named MVP while slugging 63 triples. This year also introduced disabled lists to the league. This was also the first year which divided the league into two divisions -- the Hanover and the Morris divisions. 1993 also saw the first All-Star Ballots. Qualifications were lowered to allow more players to qualify.

In 1994, Vancouver became the first team to win back to back championships. Juan Gonzalez tied Roger Maris' old home run mark with 61 homers to win the MVP award. The Scranton Sparrows became the Louisiana Lightning.

In 1995, the season was cancelled and the future of the league was in doubt because of the Major League strike.

In 1996, the league resumed as three teams folded -- Tampa Bay, Charleston, and Waikiki -- and three teams joined the league -- Jerusalem Rabbis, Newark Sugar Bears, and Toledo Mutthens. Cheyenne also was taken over by Mark "Tex" Zidiak and renamed the Norfolk Ewes. Mark McGwire shocked the league by smacking 84 home runs.

1997 marked the first year of using Diamond Mind to play the season's games. Kenny Lofton took advantage and shattered the stolen base record by more than 50 steals. 1997 also welcomed four new teams: Chris Pucci's Carolina Mudcats, Mike Chan's Phoenix Dragons, Adam Kozubal's Honolulu Sharks, and Paul Barbosa's Lisbon Diabos. The first major-league style expansion draft took place, instilling the pre-draft 15 man protected lists. Qualifications were once again lowered to allow more players into the pool. Also the number of playoff teams was increased from four to six. Scheduling was changing to include more games against the divisional opponents. Newark became the first team other than Arkansas and Vancouver to win a championship. Alex Rodriguez was taken with the first draft pick.

In 1998 three owners were replaced -- Walt Zieser (New York Mets) replaced Daryl Melillo, Scott Boehler (Hillsborough Destroyers) replaced Tex Zidiak, and Anthony Pucci (Philadelphia Eagle Wings) replaced Paul Barbosa. Late-season roster expansion was also introduced. Nomar Garciaparra was taken by Phoenix with the first draft pick. Mark McGwire challenged his own home run record, but fell short with a "mere" 70. The Arkansas Falcons stymied the Iron Fist in the championship, four games to two. Mark McGwire was named MVP and Greg Maddux, winning his 100th career game, won the Cy Young. Nomar Garciaparra of Phoenix was awarded the first Rookie of the Year Award. 1998 also featured two firsts: the first league no-hitter, thrown by Juan Guzman and Mel Rojas of New York; and the first player to hit for the cycle: Todd Hundley of Toledo.

In 1999, Rob Hammer (Keystone Gamblers) took over for Brent Campbell, after two unsuccessful purchases of the franchise. Also, Mike Day (Hawaii Volcanoes) took over for Walt Zeiser. El Duque was taken with the first pick of the draft, which was conducted online for the first time in league history.

In 2000, Mike Day's "brother" took over for Brent Campbell, renaming the team Arizona Rattlers. After the season, it was found out that Day was controlling two teams and was ejected from the league, marking the first time in league history that a member was expelled from the league. Paul Barbosa also returned to take over for Jon Knowsley's team, calling his team the Kentucky Hillbillies. This year was the first year that the division title was decided by a one game playoff. Arkansas defeated Vancouver in the 163rd game of the year.

In 2001, Jeremy Berger (Vatican City Cardinals) took over for Scott Boehler and Mark Hrywna (Hoboken Cutters) and David Schlossberg (Brooklyn Bean Counters) held an expansion draft from rosters of the two formerly Day-owned teams. Eric Wickstrom (Harrison Rats) took over for long-time owner Steve Zajac. This year marked the introduction of the This Week in DMBL series of articles. Randy Johnson pitched the first complete game no hitter in league history this year.