My fantasy version of WM 9 was always the most unrealistic way possible to do it, but Ideally I had Bret, Perfect, and Yokozuna going over Hogan, Flair, and Macho Man in the top 3 matches and setting up the "new (yes I realize Perfect and Bret are mid 30's) generation. I also disregarded some irl issues like Marty Jannetty's problems. My card usually went:
Hulk Hogan vs Bret Hart for the WWF Title
Ric Flair vs Mr. Perfect in a Loser Leaves Town Match
Yokozuna vs Macho Man Randy Savage
Shawn Michaels vs Marty Jannetty for the WWF Intercontinental Title
The Undertaker vs Razor Ramon (I don't think losing to Taker would hurt Razor that much as his face turn was inevitable either way. It would be as good as a match as Taker could have in the 1993 version of the gimmick)
The Steiner Brothers vs Money Inc for the WWF Tag Team Titles
Bam Bam Bigelow vs Tatanka (Schmoz finish to protect both guys)
Lex Luger vs Owen Hart (Competitive squash and Owen would make Luger look fantastic)
Doink The Clown vs Bob Backlund (Idk, I think this would be weird and interesting)
The Headshrinkers vs The Nasty Boys (Put the Shrinkers over in a good brawl)
Not realistic, but I wish it happened. I apologize to the Crush heads, but he's in the dark match squashing The Model.