2002 - 2005: The Introduction of the Cup Inspires New Levels of Competitiveness
Karen Torres won the championship in 2002, and Suzanne Smith, wife of long-suffering statistician Tom Smith Jr., took the crown in 2003. Suzanne was the first recipient of the Diffendorf Cup, a trophy now presented annually to the league victor, who gets to keep the Cup for a year, until a new winner is declared. All previous winners' names are engraved on the Cup.
In 2004, doubtless spurred on by the allure of the newly introduced Cup, Tom Smith Sr. became the League's first 3-time champion, marking the 10-year anniversary since his last championship. This victory also marked the end of a duly-noted five-year championship drought for the men of the League. Ray Sullivan, perennial Commissioner of the League, took home the Cup after the 2005 season.