15 Biggest Matches WWE Should've Booked In The 90s (But Didn't)

10. Sycho Sid vs. Stone Cold Steve Austin (1997)

Sycho Sid's role at the 1996 Survivor Series in Madison Square Garden helped usher in the Attitude Era and forever changed the career of 1996 King of the Ring, Stone Cold Steve Austin. As '96 came to a close, WWE began booking more heel vs. heel matches. Battles between Steve Austin and Hunter Hearst Helmsley, Steve Austin and Vader, and Mankind and Vader all marked a shift in booking strategy for the company that usually avoided like-sided matches. Austin did battle Sid in a February '97 match on RAW, but it was a throwaway contest that went nowhere. Following WrestleMania 13, Sid was set to feud with Bret Hart while Austin would eventually be put against Brian Pillman. Despite being given the world title in late '96 and again in early '97, Sid had become unreliable by mid-'97 and once again found himself out of the company by summertime. Austin would go on to become the biggest superstar in WWE history. It's not the biggest missed opportunity, but given these two men's similar personas and their loyal, massive fan bases in '96 and '97, a Sid vs. Austin program would've been one to be remembered.