6. Triple H Vs. Booker T - WrestleMania XIX & SummerSlam 2007
When Triple H, Ric Flair and Jerry Lawler started making borderline-racist comments in regard to Booker T's troubled past (he served nineteen months in prison after a string of armed robberies), most fans and insiders assumed that 'The Book' had to triumph over The Game at WrestleMania XIX. Booker had a tonne of momentum and was as over as he's ever been following his revelations. It empathised him in the eyes of the fans, the same way Eddie Guerrero's addiction promos would a year later. Booker was a hell of a worker and, after a pretty dismal title reign, many felt like it was time that Triple H surrender the title. Sadly, it was not to be. Even worse, the manner in which Triple H won was deeply insulting: after absorbing a rare Harlem Hangover (which should have been the finish), Triple H got to his feet first, hit one solitary pedigree, lay on the mat for a good eighteen seconds and then finally made the cover. He had pinned Booker cleanly, which gobsmacked fans. Worse, the match was only average. Still, Booker would have taken a long, average match over the glorified squash he got at SummerSlam 2007. Triple H was returning from a torn quad (another one) so the result was never in doubt. But the manner of the defeat (Booker was pinned inside eight minutes by a considerably less muscular Triple H) was a deciding factor in Booker leaving the company just a few months later.