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Let's assume yes to both.
The Daleks could swarm the Borg with sheer numbers and killing rage, but the Borg could, just as easily, assimilate the Daleks to create Dalek-Borg--a truly terrifying prospect. I think that the Dalek-Borg would be superior to both and would wipe them all out.
Winner: Both lose.
But you are forgetting, Daleks are Daleks only. As soon as one is assimilated they are corrupted. Just like in the first season when Rose changes the Dalek, he no longer wanted to live. I think you would encounter a similar scenario. Though since Borg's do not have emotions either it wouldn't get all sad but it will be conflicted. It would be torn between it's original program to exterminate and the new one, to assimilate. It wouldn't understand what to do, to exterminate means it can't assimilate but to assimilate means it can't exterminate. Therefore a Dalek-borg would be completely useless. Also assimilating someones takes a lot of time and unless they figure out a way to knock the Dalek unconscious there would be no way to go through the process of implanting all the Borg technology.
Honestly there are too many variables to decide a clear cut winner. I'd say, they both are awesome in their own ways and if they ever meet. That would be an epic battle of epicness.
3nodding