http://bugs.winehq.org/show_bug.cgi?id=12289
--- Comment #3 from Reece Dunn msclrhd@gmail.com 2008-03-30 06:04:33 --- What are your window manager behaviour preferences?
I know that I have had strange menu behaviour due to window managers interacting with Wine. Have you tried running notepad in a Wine desktop, or letting Wine do the rendering of the controls? (NOTE: both of these options are on the 'Graphics' tab of winecfg.)
NOTE: I am running Ubuntu Gutsy (Gnome).