Ok so, so far during this tournament I've mostly voted on who is the "bigger star" and would logically be booked to go over in this tournament. Let's address that first.
Yes, Jeff Hardy reached a higher peak than Owen Hart. He got more over (probably, Owen was a great heel during late 1994 but faltered) and won the big one. We can't begin to guess whether Owen would of won it, so we won't. It's irrelevant. It didn't happen, Hardy went higher on the card, drew more and had a bigger career.
Usually thats enough for me, but this match is interesting - because I strongly feel this is exactly the type of match Owen Hart would win. Vs a super popular babyface that he can be a huge douche against. Let's look at this in more detail within kayfabe.
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There isn't a ton of wrestlers like Jeff Hardy in the WWE at this time. The best I can find is a young X-Pac here. It's exactly the way I see this going down though, Owen bumping around like a lad and making Hardy look great before capitilising on a mistake.
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He had Shawn Michaels beat clean here - that's a pretty big deal during Shawn's absolute prime.
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Just to be balanced, here he loses to shawn but considering Shawn is one PPV away from main eventing Wrestlemania 12 for the biggest moment of his career, and is being booked as strongly as possible, it's SUPER competitive. And this is a tougher opponent than Jeff Hardy ever has been or ever will be, bear in mind.
Now Jeff.
He's 4-1 down lifetime to the Xpac. 4-1 down, as a face vs a heel. Sure, he's not in his peak though ok.
Prime Hardy was booked superrrr strongly vs the roster and was pretty much the #2 babyface in the WWE. Vs Triple H he had a win/loss over this time of 4-2 in Jeff's favour. Vs Randy Orton, he went 3-3. Both of those are massive, massive heels in the WWE.
The guy whose workrate was most similar to Owen Hart in the main event picture at that time? CM Punk. CM Punk was absolutely nowhere near the level he has reached now. He had just turned heel, was slowly getting over but he hadn't even won his first WWE title. My point is, CM Punk was no Orton or HHH at this stage, not by any means, and yet he repeatedly won the pay off match vs Jeff Hardy and had an overall 4-3 record over Jeff.
This is the most technical guy Jeff faced. He had more luck against a near prime HHH than him, while Owen has always excelled against highflyers.
Look, if you wanna pick who is the bigger star, who has achieved more, who deserves to go through, this is a no-brainer for Jeff Hardy. An absolute no brainer.
But when I consider this match, all I see is Owen Hart getting in Jeff Hardy's head and capitlising on a mistake to get into the second round.
Also, logically - why on earth would they put Jeff Hardy through to face Andre the Giant in the 2nd round?! Of courseee they would book Owen through, that match works roughly 19309311x better.
I dunno. Just throwing it out there. You can't go wrong with either man here and Jeff deserves it. I just think Owen would win in kayfabe.