Thrilling championship games have become a hallmark of the Junior League World Series. The 1998 world champion from the South Mission Viejo Little League from California won a dramatic final-day doubleheader against the Midway Little League from Waco, Texas. Ashton White, son of former Heisman Trophy winner Charles White, was one of the top players for California.
In 1999, two major changes took place. For the first time, the Junior League expanded to include older players, 14-year-olds. The expansion led to the first-time participation in the World Series by a team from the Far East region, Guam, and would allow for more nations to compete in regional tournaments worldwide. That Far East region would eventually expand and be renamed the Asia-Pacific region.
The 1999 champion was the Hermanos Cruz Little League of Arroyo, Puerto Rico, which defeated a team from Amistad y Deporte Little League in Hermosillo of Sonora, Mexico, 1-0, in the final game of the World Series. It was the fifth time a team from Puerto Rico won the Junior League world championship, but the first title for Arroyo.
In 2000, a team from Canada – Langley, British Columbia – made it to the finals for the first time. However, Aiea took home the world title to Hawaii for the first time in 16 years.