| Monday, Nov 30th |
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| | Mon, Nov 30 7:30 pm | Girls Varsity Basketball |  | Boone High School Conference Game | Home Windermere High School | 7:30 pm | | Event Canceled Event Details |
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| Tuesday, Dec 1st |
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| | Tue, Dec 1 7:30 pm | Girls Varsity Basketball |  | Edgewater High School Conference Game | Home Windermere High School | 7:30 pm | | Event Canceled Event Details |
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| Thursday, Dec 3rd |
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| | Thu, Dec 3 6:00 pm | Girls Varsity Basketball |  | Olympia High School Conference Game | Home Windermere High School | 6:00 pm | | Event Canceled Event Details |
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| Tuesday, Dec 8th |
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| | Tue, Dec 8 7:30 pm | Girls Varsity Basketball | | Evans High School Conference Game | Home Windermere High School | 7:30 pm | | Event Details |
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| Thursday, Dec 10th |
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| | Thu, Dec 10 7:00 pm | Girls Varsity Basketball | | Dr Phillips High School Girls Basketball Conference Game | Away Dr Phillips High School | 7:00 pm | | Event Details |
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| Monday, Dec 14th |
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| | Mon, Dec 14 7:30 pm | Girls Varsity Basketball |  | Apopka High School Conference Game | Home Windermere High School | 7:30 pm | | Event Details |
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| Wednesday, Dec 16th |
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| | Wed, Dec 16 6:00 pm | Girls Varsity Basketball |  | Haines City High School Conference Game | Home Windermere High School | 6:00 pm | | Event Canceled Event Details |
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| Friday, Dec 18th |
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| | Fri, Dec 18 6:00 pm | Girls Varsity Basketball | | Ridge Community Senior High School Conference Game | Home Windermere High School | 6:00 pm | | Event Canceled Event Details |
| | Ridge Community Senior High School | | | |
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| Tuesday, Jan 5th |
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| | Tue, Jan 5 7:30 pm | Girls Varsity Basketball |  | Ocoee High School Conference Game | Away Stadium @ Ocoee High School | 7:30 pm | | Event Details |
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| Thursday, Jan 7th |
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| | Thu, Jan 7 6:30 pm | Girls Varsity Basketball |  | Timber Creek High School Conference Game | Away Timber Creek | 6:30 pm | Loss 79 - 61 | Event Details |
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| | Thu, Jan 7 6:30 pm | Girls Varsity Basketball | | Timber Creek High School Conference Game | Away Timber Creek High School | 6:30 pm | | Event Details |
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| Tuesday, Jan 12th |
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| | Tue, Jan 12 7:30 pm | Girls Varsity Basketball |  | Wekiva High School Conference Game | Home Windermere High School | 7:30 pm | | Event Details |
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| Tuesday, Jan 19th |
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| | Tue, Jan 19 7:00 pm | Girls Varsity Basketball | | South Lake High School Conference Game | Home Windermere High School | 7:00 pm | | Event Details |
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| Thursday, Jan 21st |
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| | Thu, Jan 21 7:30 pm | Girls Varsity Basketball |  | West Orange High School Conference Game | Away West Orange High School | 7:30 pm | Loss 46 - 38 | Event Details |
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| Monday, Jan 25th |
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| | Mon, Jan 25 6:30 pm | Girls Varsity Basketball | | St. Cloud High School Conference Game | Home Windermere High School | 6:30 pm | | Event Details |
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| Thursday, Jan 28th |
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| | Thu, Jan 28 7:30 pm | Girls Varsity Basketball |  | Jones High School Conference Game | Away Jones High School | 7:30 pm | | Event Details |
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| Thursday, Feb 4th |
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| | Thu, Feb 4 7:00 pm | Girls Varsity Basketball | | Osceola High School Conference Game | Home Windermere High School | 7:00 pm | Win 65 - 35 | Event Details |
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| Friday, Feb 5th |
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| | Fri, Feb 5 7:00 pm | Girls Varsity Basketball | | Haines City High School | Home Windermere High School | 7:00 pm | | Event Details |
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| Thursday, Feb 11th |
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| | Thu, Feb 11 7:00 pm | Girls Varsity Basketball |  | Lake Nona High School Conference Game | Home Windermere High School | 7:00 pm | | Event Details |
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| Tuesday, Feb 16th |
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| | Tue, Feb 16 7:00 pm | Girls Varsity Basketball |  | Oak Ridge High School Conference Game | Home Windermere High School | 7:00 pm | | Event Details |
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