Ovinomancer
No flips for you!
It's good that you acknowledge that you'd rule this situation having uncertainties and therefore use the resolution mechanics. That's a valid approach.He's a 5th level Fighter with 50 odd hit points (who only dies at 0 HP when 50 or more damage remains, or he fails 3 death saves).
The assassin needs to:
1) Hit the Fighter (with advantage most likely) against the Fighters AC. Likely but not certain.
2) Deal enough damage to kill the fighter against those HP, or at least reduce the Fighter to 0 HP in order to finish the job off once he's at 0 HP. Not certain.
The outcome of a hostile action against a PC (or anyone for that matter) is almost never 'certain'. Unless we're dealing with an NPC that can 'auto hit' somehow and 'auto kill' with the amount of damage he deals against the PCs HP, it's not certain. Not even close to certain.
Equally valid, however, is deciding that a sleeping target unaware of the assassin is going to have a hard time living with two feet of steel through the ear and that, given the target is sleeping and unaware of the assassins positioning the blade, that uncertainty isn't part of the equation. Really, the only issues here are how this situations is obtained. I'd never do this to a PC with an NPC because, well, frankly I have infinite dragons and don't need to be a jerk and abuse the game to fiat this into existence. I'd definitely let a PC do this to an NPC, but they'd have to pass all of the necessary checks to get there first.. I don't see the need to add a combat at the end of a careful approach full of successful checks. If the PC has already earned getting into that position, I'm quite okay with thinking that things aren't uncertain anymore. I think that this needs to be looked at as well, rather than just postulating a jerk GM being magically stymied by a strict application of the combat rules. The GM's still a jerk, and that won't stop them.