Is this kind of grouping possible for Silverlight DataGrids?

The first three rows of the first column are combined into one block because their data are the same.
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No, the default Silverlight datagrid control does not support this kind of grouping, however you can achive a similar result using template columns:
First you should create a Class that would contain the grouped data, something like this:
Then bind your DataGrid to a collection of
MySourceClass(or whatever name you call it), and create aTextColumnfor Column1, and aTemplateColumnfor Column2 with aListBoxor similar, and bind the source of theListboxto theGroupedColumnproperty.You might have to thinker a bit with the styles, but i’m pretty sure you can acomplish a solid look with this aproach.
EDIT:
Alternatively you could use the default DataGrid grouping, her’s a good example for it:
http://www.codeproject.com/Articles/134340/Grouping-Records-in-Silverlight-DataGrid-using-Pag