#2 Kurt Angle vs Triple H
Triple H is the Executive Vice President of Talent, Live Events and Creative for WWE and makes sporadic television appearances. Kurt Angle, on the other hand, is the current Raw General Manager.
On November 19, 2017, at the Survivor Series In the main event, Team Raw (Kurt Angle, Braun Strowman, Finn Bálor, Samoa Joe, and Triple H) faced Team SmackDown (Shane McMahon, Randy Orton, Bobby Roode, Shinsuke Nakamura, and John Cena) in a 5-on-5 elimination match, with the stipulation being that if Team Raw were to lose, Angle would be fired as Raw General Manager. In the final moments of the match, as Angle had Shane in the Angle Lock, Triple H turned on Angle and performed the Pedigree on him and then placed Shane on top of him to eliminate Angle. Triple H did this to claim credit for Team Raw's victory as he performed the Pedigree on Shane to eliminate him and win the match.
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There is no love lost between these two legends who are both healthy enough and in good physical condition to put on a good match. They have faced each other multiple times in the past and so they know each other too well. Kurt Angle is yet to revenge on Triple H following The Game's actions at Survivor Series. An "Angle Slam" on an unexpecting Triple H could be on the works to set up a dream match between the two.
Lest we forget, there was even a time in 2000 when the two had a feud over Stephanie's affections.