7 Wrestlers Shawn Michaels Refused To Lose Against
5. Owen Hart

The Montreal Screwjob may have taken place on one fateful night in November, but the Hart family screwing didn't end on that night in Quebec. Bret, Jim Neidhart and Davey Boy Smith all left the company, but Owen Hart was stuck in a contract he couldn't get out of. Arguably the most talented of the bunch was stuck in his prime in a company he had legitimate animosity with.
Owen returned with pure babyface fire to attack Shawn in December of 1997, and a simple story was sat in front of Vince McMahon & Co. Owen should essentially have become a DX Hunter (no, not Yoshitatsu), picking off member after member before finally getting his hands on Shawn Michaels.
Instead, Owen was transitioned into a long feud with Triple H as Michaels continued working with Undertaker over the beginning of the year. The rumour was that Michaels had no interest in working with and losing to Owen, most likely because he was convinced Owen would stiff him.
You know, due to that whole screwing over his big brother thing.