25 Days Until WWE Wrestlemania 28
The first time these two came face to face in the 2005 WWE Royal Rumble. Shawn Michaels eliminated Kurt Angle and Angle retaliated by beating up the Heartbreak Kid. It was a savage beating to say the least. Kurt Angle would set the stage, he would do everything that Shawn Michaels woudl do. He had a match with the old Rockers team mate of HBK, Marty Jannetty, that was so good that it got Marty a deal with WWE, at least for a short time. Kurt Angle also brought out the old manager of Shawn Michaels from back the day, Sensational Sherri and sang their own variety of the old theme song of the Heartbreak Kid's Theme Song "Sexy Kurt". Then Kurt Angle beat up Sherri and put her in the Ankle Lock. Chivalry is dead.
WWE Wrestlemania 21, it happened between Kurt Angle and Shawn Michaels. And it was another banner Wrestlemania performance from Shawn Michaels. As for Kurt Angle...this match began a good portion of the fanbase to turn on Kurt Angle and pick apart his work. And to a lesser extent Shawn Michaels as well. To be fair, the degrade of Kurt Angle really didn't start until about 2006 and he does have his moments of good wrestling.
And this was a great match, even if their match later that year at Vengeance 2005 might have been a bit better. But Kurt Angle and Shawn Michaels stole the show at Wrestlemania 21, with the match of the evening. After some back and forth action, Kurt Angle slapped on the deadly heel hook Ankle Lock and tapped out Shawn Michaels. Kurt Angle was your winner and he was set up for a huge feud with John Cena, the next big superstar in WWE(remember when John Cena getting pushed down our throats in WWE was something new and fresh?) Yet Shawn Michaels would have many more matches.
Three years later, Shawn Michaels took on another one of the all time greats in wrestling history and as Shawn Michaels week continues(or more like Shawn Michaels nine days). We have 25 Days and Counting to WWE Wrestlemania 28.