I think this is a match more suited for Bret Hart's style than Warriors, particularly the three type of matches for each fall. I definitely don't think that Bret could pin Warrior two times out of three matches. No do I think Warrior would submit either. But you don't have to win by pinfall or submission in a Ladder Match, nor a Cage Match (though you can in that case, but you don't have to), which works in Bret's favor.
Bret is smart and crafty in the ring as he's proven so many times. He played possum on so many guys and and pinning them out of nowhere with crafty roll-ups, or moves no one would've thought of. And his strategy in matches is second to none. He always had a game plan and was always a step ahead in the ring, no matter how good his opponent was. Bret would easily outsmart the Warrior. It's just a matter if Warrior would beat Bret quickly and easily.
I think ultimately Warrior would win the Street Fight, as this is the match where the winner has to win by pinfall, and Warrior was pinned far less than Bret. Bret would put up a fight but Warrior would win. As crafty as Bret is, he would probably try to wear Warrior down with submissions, particularly with Warrior's legs. But in the end Warrior win. This would not be a quick 2-3 minute match like others are saying. For those thinking Bret is just a technical wrestler and couldn't win a Street Fight, look at his Submission Match at WM 13 against Steve Austin (which he won). Look at his match at In Your House with Davey Boy Smith that was No DQ. Davey his similarly powerful to Warrior. Bret won that one. And then there's the title match against Diesel at Survivor Series. Another No DQ match, against a guy much bigger than Warrior. Bret won that one too. Bret would put up a good fight, but ultimately lose.
Then we're onto the Ladder Match. A brutal match that Warrior never wrestled in and that Bret originated. But more importantly, no pinfalls or submissions. This match, is all about craftiness and the ability to climb the ladder. All Bret has to do is wear Warrior's legs down (which he would more than likely do in the Street Fight), and he could tie him up in the ropes, just long enough for him to climb the Ladder. Or something crafty like that. Bret would do anything to win, and that's exactly what he'd do here.
Then we get to the Cage Match, a match that both were successful at, particularly at Summerslam. As Warrior beat Rick Rude at Summerslam 90 in the cage, and Bret did the same to Owen Hart at Summerslam 94. This would probably be the most even match, as by the time this fall takes place, both men will be extremely worn out (Warrior probably moreso). Bret has the advantage though as he doesn't have to pin Warrior or make him submit. He can climb to escape the cage or leave the door. Warrior obviously can too. But in the end, I could see Bret finally getting the sharpshooter on Warrior. Warrior starts to power out of it, but Bret doesn't let him and puts the Sharpshooter back on. This time Warrior doesn't get out of it and passes out. The ref can either stop the match and award it to Bret, or Bret simply lets go and exits the cage, advancing in the tournament.
Bret should win this.
