I tried deleting the history on my computer, the app, uninstalling the app, signing out, uninstalling skype on my computer, any other suggestions to get rid of the chat history?
Hurrah, I finally figured it out. When the Messages list is open on the ipad, run your finger along the item (left to right), and a red "delete" button will appear.
This does really suck. Before recent iphone and ipad application updates were released, all you had to do was swipe a conversation in your history or messages list and hit delete. Doing that deleted the item and it did not reappear the next time you started the app.
My iphone app now returns every conversation from Sept 30 onward and the history of my ipad app is hanging onto everything dating back to Sept 13. If I checked my purchase/sync history or whatever it would be called in itunes, I am sure it would show that I downloaded an update for iPhone Skype on Sept 30 and that I installed iPad Skype on Sept 13 (previously I was using the iPhone only version on my iPad).
So if I was able to permanently remove history before the updates and now I cannot, that would make the moderator's post that said it was "currently not available" a **bleep** lie. It was available but your development group "broke" it because of a crappy QA process. I can't believe how quickly you guys have adopted the Microsoft culture of "beta testing in production". Freaking typical.