I think this may reduce to a question of whether you can programmatically write to the UIWebView's cache file (which is to say, whether the UIWebView cache resides within your app's sandbox) – if you can't, then game over. If you can, then it becomes a question of what happens after you drop a pre-populated cache file into place, and whether the UIWebView is "fooled" into thinking that it's already downloaded and cached your HTML5 content.
If you're using the iPhone Simulator to test your app, look in ~/Library/Application Support/iPhone Simulator/5.0/Applications
(replace "5.0" with your iOS version, if necessary). You should see a long string of hex digits for each app you've compiled in the simulator; find the one that corresponds to your app, and then look in the Library/Caches/[your app's identifier]
subfolder for a file named Cache.db
.
This may be the place where UIWebView stores its cache data. If it isn't, game over and the answer to your question is "no, that's not possible". If it is where UIWebView caches data, then it may be possible to populate this Cache.db
file in the simulator, grab the file, store it in your app bundle, and then write the cache to the appropriate location when it's time to pre-populate the cache.
At any rate, that's the line of attack I'd use to determine whether it's possible – I'm pretty confident the answer is going to be "no, not possible" unless it turns out the UIWebView cache does reside in your app's sandbox, is writable by you, and you can fool UIWebView by replacing its cache file.
UIWebView
from the documents directory of your app. – Discourteous