Tech levels

I was just wondering:

What would happen if the western air forces met an enemy that was:
1- as modern as themselves. Until today, the west always had a technological advance. It was almost sure that they would win: they had shiny, brand new things, the enemy old, mostly soviet stuff that hardly flew. But what if the west would meet an enemy that had stealth, UCAVs, great radar,…
2- really old and small. Isn’t there a danger that the west will be too high tech? If it ever meets an enemy that isn’t interested in a full-scale war, will it be able to survive. You could use Somalia and Vietnam as examples. Could the west survive in a ‘dirty’ war?

In other words: is our technology still ready for the world? Is the technology difference not getting too big?