Owen was a tough S.O.B., there's no doubt about it. He was a good performer and worked his ass of to emerge out of the shadow of his older brother for the entirety of his career. He lived up to the legacy of the Hart name, and despite being the youngest of all the Hart children he proved his weight in the squared circle. He was never Bret, but to be fair Owen was never really given that chance, before or after his death.
That being said, I've got several reasons Eddie Guerrero wins this contest:
1.) First, and possibly most important of all, this "match" is being billed from Dallas, TX. There's no way that Eddie Guerrero loses a match in a huge tournament, in the first round, right outside of his hometown.
2.) In a technical match, you would think just about any Hart would have the upper hand, but Eddie was one hell of a technical performer. Better, in my opinion, than Owen.
3.) His speed and agility, plus a touch of the lucha style makes Eddie too quick and slippery for Owen to do much of anything.
4.) Eddie is a former WWE Champion, not to mention his Triple Crown and Grand Slam status. While "anybody" can win a title, this just proves Eddie knows how to come through in big scenario situations...like the first round of a prestigious tournament.
5.) Eddie Guerrero is one of the few to have defeated Brock Lesnar. Every other competitor just looks kind of easy in comparison.
6.) Eddie has defeated guys that wrestle with just about every style. Lucha, technical, heavyweights, super-heavyweights, monsters, cruiserweights, etc etc.
7.) If ALL else fails and Eddie somehow finds himself losing to Owen in the final moments of the match, he can ALWAYS cheat to win.
Viva La Raza!