news | March 25, 2026

The Definitive List of Must-Watch Matches from WWE Hall of Famer Shawn Michaels | News, Scores, Highlights, Stats, and Rumors

Imagine working with your idol; the person responsible for shaping you into the person and professional you are today. Few people ever have that opportunity, even fewer on the most significant stage in their field.

That was the position Michaels was in at WrestleMania XXIV in 2008.

The Heartbreak Kid had competed against Flair before, but with the added element of The Nature Boy's career being at stake on the WrestleMania stage, pressure was on to deliver a match befitting the enormity of the moment.

Flair put in the work, but it was a one-man show as Michaels strove to give his childhood hero the match he deserved in what would be his final outing as an in-ring performer in WWE. All while nursing cracked ribs suffered early on following a missed top-rope moonsault that saw him land on the edge of the commentary table.

Shaking off the bumps, bruises and certain agony, Michaels rocked his mentor with Sweet Chin Music. When the defiant Flair stood, fists clenched and dared his opponent to put him down, Michaels obliged, but not before telling him he loved him and that he was sorry.

The emotional storytelling of this match trumped any physicality. From an action standpoint, it was a very basic match. But the story that Michaels and Flair told on that night resonated with fans, leaving them teary-eyed at its conclusion.

For a performer whose legacy is defined by his storytelling prowess, this ranks among Michaels' very best.