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I'm not using cache function yet, but you can try with the new version of the listener - 2.0 EA2 ?
this is still the same with the current EA2 for APEX Listener 2.0 - the embedded Grizzly doesn't provide a caching mechanism for the static ressources.
On the other hand, the Standalone Mode is intended to be used for development purposes, so you usually won't actually need and sometimes even don't want to have caching.
thanks for the clarification.