9. Big Show Vs. Brock Lesnar
Back in 2002, Brock Lesnar was on an unforeseen tear, winning the WWE Championship just five months after his explosive debut. He was universally considered the next hot superstar of wrestling, one who could potentially define the future of the WWE. He suffered his first pinfall loss just two months later.
The fact that Brock lost his title to the Big Show, rather than a top-tier star such as Kurt Angle or The Undertaker, makes such a booking decision all the more baffling. Show benefitted from the betrayal of Lesnar's manager, Paul Heyman, to win the title at Survivor Series, only to then drop the belt to Angle at the very next PPV.
Lesnar fortunately lost little momentum, winning the Royal Rumble and regaining his WWE Championship at WrestleMania XIX. However, his loss to Big Show remains a curious blip at the start of an otherwise mightily impressive run at the top of the wrestling world.