In sikuli, if you want to simulate pressing and holding one button, while then typing another, use type(TheKeyDoingTheAction, KeyModifier.TheKeyYoureHoldingDown
It's written like this:
type(Key.UP, KeyModifier.WIN) #This is the one from your question
Here are a few other common examples:
type("c", KeyModifier.CTRL) #copies whatever is selected to the clipboard
type(Key.LEFT, KeyModifier.ALT) #goes back one page in most web browsers
Here's an exerpt from the sikuli docs:
"The modifier constants can be combined to the modifier parameter by either using “+” or “|”, if more than one key modifier is needed.
type(Key.ESC, KeyModifier.CTRL + KeyModifier.ALT)
# or equivalent -
type(Key.ESC, KeyModifier.CTRL | KeyModifier.ALT)
They should only be used in the modifiers parameter with functions like type(), rightClick(), etc.
They should never be used with keyDown() or keyUp()."