ok, from the doc of Robot
class, just do:
r.keyPress(KeyEvent.VK_WINDOWS);
r.keyPress(KeyEvent.VK_R); // VK_WINDOWS key still pressed
r.keyRelease(KeyEvent.VK_R);
r.keyRelease(KeyEvent.VK_WINDOWS);
the keyPress
method does not relese the key, so this should work