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Fall Season

The Fall 2014 season registration dates will be held at George Bailey Field during the following dates:

  • Wednesday 8/20 6-8pm
  • Saturday 8/23 10-1
  • Thursday 8/28 6-8pm
  • Tuesday 9/2 6-8pm

Skill evaluations will be on 9/6 and make up on 9/8. Opening Day is October 4.

Post Season


Congratulations to the Windermere Little League teams who have competed in post-season tournaments. 


A special congratulations to our tournament winners.


All Stars


9-10 National League team and Coach Kowalski are District 14 Champions


Senior All Stars and Coach Molina are District Champions


Junior All Stars and Coach Anish are District Champions


9-10 Softball All Stars and Coach Janata are Section 5 Champions


10-11 Softball All Stars and Coach Campopiano are Section 5 Champions



Top Team


AAA Pirates and Coach Kowalski are the District 14 Minors Top Team champions.


The Reds under Coach Molina are District 14 Seniors Top Team champions.




Coach Simpson’s 9 Year old National team are the winners of the District 14 Tournament of Champions.

Our Divisions

Windermere Little League has baseball, softball, and tee ball programs for boys and girls who live within our league boundaries.  For those residing outside of our boundares we recommend the excellent Little League programs of our neighboring leagues in Ocoee, Winter Garden, Dr. Phillips, and South Lake.

We have baseball divisions for boys or girls from ages 7 through 16.  Our softball program includes girls from ages 7 through 12.  For the younger players we have a Tee Ball program for boys or girls aged 5 or 6.

Are you new to Windermere Little League?

As a chartered Little League we are assigned boundaries that define the area from which we can draw our players.  When new players register we confirm that they reside within our boundaries.  Outside of our boundaries are several excellent Little League programs.  If you live outside of our boundaries but don't know which league you are part of please visit the District 14 website.

Not sure if you live in within our boundaries?  The map below shows approximately where our borders are.  The blue markers show the locations of our home fields. Click
here if you cannot see the map of the borders of Windermere Little League below.

View Larger Map

Driving Directions to the Fields 
Click here for driving directions to our fields:

Windermere Elementary

George Bailey Park


Several businesses and organizations have partnered with Windermere Little League in providing our community with a fantastic baseball program. We encourage you to visit our sponsors and support their commitment to our program.

• Some Other Great Sites

Go to our links page for a list of useful websites that contain a wealth of information about little league baseball and softball.

For further information please email contact@windermerell.org.

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