About Windermere Little League

Windermere Little League is part of Florida District 14 which includes the leagues from the following communities: Dr. Phillips, MetroWest, Pine Hills, Rolling Hills, South Lake, Winter Garden, and Windermere.

There are currently 25 Districts in the state of Florida.

For complete coverage of Little League Baseball at the Majors League Level (ages 11-12), be sure to visit Unpage Publications.

Florida is part of the Southeast Region of Little League.

League History
If you have information regarding past history of Windermere Little League, please contact us and let us know!

In 1987, Windermere’s Majors all-star team was District 14 champion.

In 2003, Windermere’s All-Star teams (Minors, Majors, and Seniors) all were District 14 champions, and the Seniors team placed 3rd in the state of Florida.

In 2004, All-Star teams from Windermere took 7 of the 9 championships for District 14 baseball and softball. Windermere’s 14-year-old All-Stars placed 3rd in the state of Florida.

In 2005, All-Star teams from Windermere took 4 championships for District 14 baseball and softball. Three of Windermere’s teams then went on to take the Sectional championships as well, advancing on to the state tournament (9/10 Baseball and 11/12 Softball).

In 2006, All-Star teams from Windermere took 4 championships for District 14 baseball and softball. The 11-year-old All-Stars took the Section 5 championship and finished 3rd in the state of Florida.

WLL Organization
Windermere Little League is divided into the following divisions:
Tee Ball (players league age 5-6)
Single-A (league age 7-8)
Double-AA (league age 8-11)
Triple-AAA (league age 9-12)
Majors (league age 10-12)
Juniors (league age 13-14)
Seniors (league age 15-16)

We also have a Girls’ Softball League for ages 7-8, 9-10 and 11-12.

The Minors (Single-A, Double-AA, Triple-AAA) and Majors divisions are further divided into American and National Leagues.

Windermere Little League plays Fall and Spring seasons. The Fall season runs September thru November; the Spring season runs February thru May. Because players generally move up divisions in the Fall, that season tends to be less competitive and more instructional in nature. The Spring season is more competitive and is followed by several Little League tournaments that our league participates in.

Windermere Little League re-drafts its teams every season.

Post-season Tournaments
There are two sets of Tournaments that Windermere Little League participates in following the Spring season.

The Top Team Tournament allows the winners of respective divisions/leagues to play the top teams from other leagues within District 14. The All-Star Team Tournament provides division/league all-star teams the opportunity to play other all-star teams within District 14. Certain age groups continue to play beyond districts up to sectionals, state, regional, and national levels. It is the 12-year-old all-star teams that play for the opportunity to go to Williamsport and the Little League World Series.

A Volunteer League
Windermere Little League is one of the largest leagues in the state of Florida with over 900 players ranging in age from five to sixteen. The only way our league is successful is through teamwork and participation. Parents serve the league in every possible way as Board Members, managers, coaches, team dads and moms, concession stand volunteers, umpires, field maintenance workers, and fund raising organizers.

We cannot accomplish our goals without the efforts of our parents. These are our players, and they deserve the best help that we can give them. Little League is a family participation sport. Without the cooperation and assistance of all involved, it will be difficult to continue to build upon the foundation already established for a strong league.

A Community League
Windermere Little League is not just about baseball. It’s about bringing community together in a family-friendly environment that encourages both sportsmanship and spectatorship. In this spirit, Windermere Little League provides a Reduced Fee Program for families in need, so that financially challenged kids can participate in a sports league that helps develop athleticism, character, and community-mindedness.