Here was my experience with dragging it to the top:

If the application started up maximized, it seems to work, but after
enough times (maybe 20 or so), it would eventually stop maximizing
correctly.  If the application wasn't maximized at startup, if would
stop maximizing correctly after only 5 or 10 times.  It also seemed to
work a better percentage of the time if I maximized/un-maximized by
repeatedly dragging the title bar to/from the top without letting go of
the left mouse button.

It would stop maximizing correctly sooner if you minimized the window OR
if you un-maximized the window by double-clicking the title bar or
clicking the un-maximize button.

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https://bugs.launchpad.net/bugs/778595

Title:
  WINE windows do not display their title bar consistently when
  maximized

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