#4 Shawn Michaels (11 WrestleMania losses)
Shawn Michaels' first two matches at WrestleMania saw him losing two consecutive tag team bouts. At WrestleMania IX, he lost to Tatanka via countout. This was followed by an Intercontinental Championship loss to Razor Ramon in 1994.
The Heartbreak Kid failed to defeat Diesel for the WWE Championship at WM XI. He lost the WWE Championship to rising Superstar Stone Cold Steve Austin at WrestleMania XIV. Michaels would go on a four-year hiatus following the loss.
Michaels won his return match at The Show of Shows against Chris Jericho in 2003. He lost at the next two events to Chris Benoit and Kurt Angle, respectively. Michaels lost a WWE Championship main event to John Cena in 2007.
At WrestleMania 25 and 26, Shawn Michaels would lose two straight matches to The Undertaker. The second one was his final WrestleMania outing.
Michaels did return for a tag team match in Saudi Arabia eight years later. He hasn't wrestled a match ever since, and it's safe to say that Michaels is done with pro-wrestling for good.