10 Best WWE Career-Threatening Matches Ever

After the apparent falling out he had with Vince McMahon in mid-2007, all signs sure seemed to point to Ric Flair retiring upon his return to Raw that November. Instead, he announced he would never retire before McMahon made it clear that he would be forced to hang up his boots for good after the next match he lost.

Thus, every match that followed for Flair was career-threatening, and although he had a handful of memorable matchups with the likes of Randy Orton, Triple H, MVP, and Mr. Kennedy, his most monumental occurred at WrestleMania XXIV against Shawn Michaels. The two had done battle before, but never on a stage quite like The Show of Shows.

Unlike other matches on this list, the ending outcome of this particular bout was fairly predictable, but that didn't make the story they told any less captivating. Flair fought with everything he had left in him even at 59-years-old, while Michaels refused to hold anything back. When it came time to put "Old Yeller" out to pasture, The Heartbreak Kid uttered five of the most iconic words in WWE history:

"I'm sorry, I love you."

Bam. Sweet Chin Music. One, two, three. The career of an all-time great had come to an emotional end, and now all that was left were memories.