1998 - 2000: The Reign of Dorothy Ruthless
The 1998 season saw family matriarch Dorothy Diffendorf claim the league title, and earn the nickname 'Dorothy Ruthless' in the process. (Never underestimate a great-grandmother.) Amanda Diffendorf won convincingly in 1999, but Dorothy Ruthless, on the strength of her beloved Yankees, got right back to the winner's circle in 2000 with a huge margin of victory (6383 - 5996).
2001: The End of 'Tough Luck'
The 2001 season marked a watershed moment for the League, because the infamous 'tough luck' policy was changed after many years of debate. The 'tough luck' policy essentially stated that you pick your roster (without subs) at the beginning of the season, and if you lost a player due to injury, being benched, being sent down to minors, etc.: tough luck.
In 2001, however, the League implemented a policy that allowed an owner to swap out two players for any reason at any point in the season. The 2001 season also set a record for the number of owners participating in the league: 37. Shannon Sullivan took the crown in this momentous season, in the closest finish in League history: Shannon held on to surpass long-suffering league statistician Tom Smith Jr. by a final score of 6796 - 6792 (a .06% differential).
2-Time Champion Dorothy 'Ruthless' Diffendorf
4-Time Champion Tom Smith Sr.