I don't think this has been confirmed, but based on some hints and my opinion I think he should have. He had negotiations/was working for Kaido, and he's got the alias "Joker" (part of Kaido's card games naming scheme).

It's been confirmed in an sbs joker was intended to be part of the beast pirates echelons

Oh I meant in the current storyline whether Doflamingo has actually met Kaido in Wano, what he's asking about. I know Oda mentioned his original purpose for Doflamingo character.

In the current storyline, he's still called Joker, indicating they've met and Kaido assigned him that alias. But I'm not sure because it could very well have been by a dendenmushi...

You can make some solid speculations that he for sure has been there for at least some face-to-face meetings with Kaido.