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This is one of the other DataGridView behavioral differences noticed between .net and mono mentioned in Bug 590.
In mono, if the DataGridView.AutoSizeColumnsMode is set, it overrides specific column AutoSizeMode settings. In other words, to get the AutoSizeMode setting to work required the removal of any DataGridView.AutoSizeColumnsMode references.
In .net the AutoSizeMode setting for individual columns overrides the DataGridView.AutoSizeColumnsMode setting which seems to be consistent with the msdn docs on DataGridViewColumn.AutoSizeMode Property which reads as follows.
"The automatic sizing behavior of the column is determined by the value of the InheritedAutoSizeMode property, which is the same as the value of the AutoSizeMode property for all values except NotSet, which indicates that the value is inherited from the DataGridView.AutoSizeColumnsMode property instead."
To see this bug in action look at the code attached to Bug ID 590. Use the CreateDataGrid() method that works and add to it a line that sets the DataGridView.AutoSizeColumnsMode to any setting and that setting will override the DataGridViewColumn.AutoSizeMode setting.