Umbra was a pushover, even a low levels with the difficulty right up. The Ebony Warrior pounded my ass repeatedly and I was level 81 with epicly enchanted gear.
Also, just as a side note, your avatar terrifies me.
Umbra from Oblivion? Like that Bosmer girl named Umbra in the Ayleid ruin who had the sword Umbra? I had zero trouble with her, I never knew she was supposed to be difficult to kill. Ebony warrior on the other hand has whooped my [censored] many times.
gaenor, without maxed agility and weapon skill that little elf would eat you alive. Somehow if that carried over to the ebony warrior/umbra fight he would curbstomp them
edit:...granted the ebony warrior would have those maxed...
Umbra from Morrowind would win over Umbra from Oblivion.... But the Ebony Warrior is overpowered and would probably kill them both.
EXCEPT...
Gaenor would kill them all.
Technically the only reason Gaenor was hard was because his luck was so crazy high, and in Morrowind, the higher your luck the harder you are to hit. And without that system he would be pretty easy to kill. But if the Ebony Warrior was thrown into Morrowind it would be a close fight.