SQL left join returns null column
You're doing the convert() in the wrong place I guess. You have to do it in the equals operation of the ON, it's still a datetime there, regardless of what you do on it in the list of selected columns.

Try:

SELECT CONVERT(date,db1.dbo.table1.datecolumn), db2.dbo.table2.datecolumn
FROM db1.dbo.table1
LEFT JOIN db2.dbo.table2 
    ON CONVERT(date,db1.dbo.table1.datecolumn) = db2.dbo.table2.datecolumn