#2 The Undertaker vs. Shawn Michaels (WrestleMania 26)
Just two years after Shawn Michaels had retired Ric Flair, this time it was HBK's turn to ride off into the sunset. After coming up short against the Phenom at WrestleMania 25, Michaels did everything in his power to get a rematch. Costing the Undertaker the World Heavyweight title proved to be the final straw, and the two met in Phoenix, where Michaels lost and was forced to retire for good.
And for many years, Michaels was true to his word as it seemed that the Showstopper would be one of the rare Superstars to stay retired. That changed last year though, when HBK teamed with Triple H to face the Brothers of Destruction at Crown Jewel, and though it was fun to see the Heart Break Kid in the ring once again, many fans believe he shouldn't have returned at all.
#1 Triple H vs. Cactus Jack (No Way Out 2000)
When Triple H retained his WWF title against Cactus Jack at the 2000 Royal Rumble event, fans knew that the war between these two was far from over. Cactus had gotten so close to winning the title for the fourth time, and was granted another shot at No Way Out, but only if he put his career on the line.
Meeting inside Hell in a Cell, the two brought out the best of each other, though it was the Game who emerged victorious once again. Though it was a sad end to Foley's legendary career, this retirement would be very short-lived, as Foley would be brought back mere weeks later, and even competed in the Fatal Four Way main event of WrestleMania 2000, where he came up short against the Cerebral Assassin once again.