The Undertaker has been regarded as one of the most tenured, respected, and accomplished WWE legends of all time. The Man from the Dark Side has been inside the squared circle for three decades and became one of the most mystical figures in the world of professional writing.

During those three decades of destruction, The Undertaker battled opponents from various eras. This includes stars like Hulk Hogan, Triple H, The Rock, John Cena, Edge, and Roman Reigns. All have delivered some of the top showdowns against The Phenom.

The Undertaker as his Deadman persona/Credit: WWE

One of his most prolific opponents was Shawn Michaels. The duo had some stellar matches against each other in their respective careers. Moreover, it was The Phenom who retired Michaels in a high-profile ‘Career vs Streak’ match at WrestleMania 26. But The Phenom recently admitted a regret regarding a superstar he calls the ‘modern-day Shawn Michaels....