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#2 Shawn Michaels vs. Daniel Bryan
Unlike others on this list, this one would have a story if it were to happen, and an interesting one at that.
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Daniel Bryan enrolled in the Texas Wrestling Academy which was being run by Shawn Michaels. He was trained by Shawn for a little while before seeking training from others throughout 2000 and moving onto WWE developmental (Memphis Championship Wrestling) towards the end of the year where he gained a large portion of his wrestling knowledge from William Regal.
When Daniel Bryan became a big star in WWE, they would often have the commentators play up how Daniel Bryan was trained by Shawn Michaels. However as CM Punk once put it while on commentary, Shawn Michaels only ever really taught Bryan a headlock and nothing more.
So going with this, as well as stemming from the promo below from 2013 when Shawn Michaels cost Bryan the WWE Championship at the Hell in A Cell event, WWE could build a really good 'Teacher vs. Student' angle.
