Well, I had problems with the "+" character that exist in the field "InstallDate". I figured it out doing some trims:
SELECT TOP (100) PERCENT YEAR(LEFT(InstallDate, 8)) AS Year, MONTH(LEFT(InstallDate, 8)) AS Month, COUNT(*) AS Installations
FROM dbo.tblOperatingsystem
GROUP BY MONTH(LEFT(InstallDate, 8)), YEAR(LEFT(InstallDate, 8))
ORDER BY Year, Month