#2 Jim Ross def. Triple H (WWE Monday Night RAW April 18th, 2005)

Some of Triple H's most shocking defeats have occurred inside the world's most famous arena. One such loss at Madison Square Garden came when legendary WWE play-by-play commentator Jim Ross won a match with The Game on Monday Night RAW in 2005.
Triple H had recently lost the WWE World Heavyweight Championship to Batista at WrestleMania 21. It was becoming increasingly apparent that The Animal had The Game's number. Triple H's frustration continued to grow with every passing week, as he was desperate to regain the World Heavyweight Championship.
Before their WrestleMania re-match for the World Heavyweight Championship at Backlash, Triple H decided to take his frustration out on legendary commentator Jim Ross on Monday Night RAW.
This feud led to a No Disqualification match in a main event at Madison Square Garden. Triple H absolutely decimated JR, causing Ross to bleed profusely from his head. Ross was without Batista at ringside because Triple H and Ric Flair had bribed Batista's limousine driver to delay The Animal's arrival to the arena that night.
But the World Heavyweight Champion arrived just in time to save JR. Batista smashed Triple H with a steel chair, leaving his former mentor motionless in the ring. Batista then dragged Ross' body and laid JR's arm on Triple H's chest. The referee counted the 1-2-3, and JR defeated Triple H in an incredibly unexpected victory.