5 Best retirement matches in WWE history 

#2. Triple H vs. Mick Foley in a Hell In A Cell Match for the WWE Championship (No Way Out 2000)

2000 was arguably WWE's most successful year ever. The company had so much momentum and had already clearly won the Monday Night Wars with WCW. They were doing marvelous in ratings, pay-per-view buyrates and merchandise. To kick off the year, Triple H was the centerpiece of the main event scene and won the WWE Championship.

He made all of the babyfaces' lives a living hell, especially Mankind. The McMahon-Helmsley Regime, headed up by The Game and Stephanie McMahon fired Mankind before The Rock organized a protest to allow them to re-hire his former tag team partner. Mankind also received a WWE Championship Match against Triple H at the Royal Rumble 2000 as well.

This became a street fight and is fondly remembered as one of the greatest WWE Championship matches of all time. The two men fought all over New York City's Madison Square Garden. They bled and brutalized one another in an effort to walk out with the gold. Mankind, under his Cactus Jack persona, was in top form, while Triple H put on a star-making performance.

The Cerebral Assassin got the win there and wanted to finally end things for good the following month at No Way Out 2000. Not only was it made a Hell In A Cell Match, but Cactus Jack put his career on the line for one last bout against his bitter rival. The intensity was extremely high going in and both men lived up to the lofty expectations going in.

The two put on a phenomenal Hell In A Cell Match that escalated in drama as the match went on. The hatred between these two was palpable and was arguably one of the best matches of a banner year for the company. Triple H retained the WWE Championship once again after backdropping Foley through the roof of the cell and the ring.

---

#1. Shawn Michaels vs. The Undertaker in a Career vs. Streak Match (WWE WrestleMania 26)

Shawn Michaels carried the end of Ric Flair's career with him for the years to follow. It was the driving force behind so many of his feuds and became a battle for him to clear his conscience. At WrestleMania 25, Shawn Michaels looked for the ultimate redemption in his mind. He faced The Undertaker and wanted to be the man to break the Streak.

It was an excellent bout that exceeded all the hype and is widely considered the greatest WrestleMania match of all time. It just might be the best WWE match ever. The loss for Michaels here drove him to insanity in wanting to get another chance against The Phenom. After costing the latter the World Heavyweight Championship, he accepted HBK's challenge on one condition.

Shawn Michaels had to put his career on the line for this rematch. This Career vs. Streak Match was the headliner for WrestleMania 26 and found a way to live up to what the two men accomplished the year prior. It was a deeply emotional encounter that felt like it could go either way. The Undertaker hit a jumping Tombstone to defeat Michaels and end his career.

The Undertaker and HBK somehow were able to have outstanding feuds in two different decades. They were the two icons who helped WrestleMania move into the stadium era. It felt big time when they stood across the ring from each other, so Michaels retiring against The Phenom was just right. That's why The Undertaker vs. Shawn Michaels is the best retirement match in WWE history.