There's still a lot of doubt as to whether Prince and Miles Davis ever recorded music together in the same studio (tracks like "Sticky Wicked" and "Can I Play With U" involved Miles overdubbing his trumpet in a different studio). Prince has said in at least one interview that he and Miles have recorded long improvisations together, but no one's ever heard any of them. Alan Leeds doesn't think so and in a new interview, Eric Leeds says the same thing.

The interview is at:
http://www.thelastmiles.c...-part2.php

Chaka Khan once said that there were plans for Prince, Miles and her to record an album together, but nothing happened - a great shame

Eric also suggests that Prince was maybe reluctant to direct Miles and, later on, might even have lost interest in working with Miles. A shame -I would have loved to have heard a Prince/Miles album!

Miles from the Park or New Years 87 the certainly jammed together.
Does this count and was it the only time they performed live together?

muirdo said:

I was talking about the two of them being in the studio together at the same time! I believe the Miles From The Park gig was the only time they ever played together, although Prince has suggested they have also recorded long improvisations together. There's something about that '87 gig in the Eric Leeds interview.

most sources only say they mailed a tape of that widely ciculating song back and forth to create the shelved "Can I Play with U?"