On Nov. 12, 1993, 2,800 spectators filled the McNichols Sports Arena in Denver for UFC 1: The Beginning. The competition featured an eight-man tournament format, with the winner taking home $50,000 as the grand prize. Royce Gracie was crowned champion with his submission of Gerard Gordeau, and the world was introduced to the Ultimate Fighting Championship. MMA, and the UFC in particular, has come a long way from that humble beginning in Denver.

Today, the UFC boasts lucrative TV and pay-per-view deals, its own reality series, and a video game franchise. Fighters like GSP and Anderson Silva have become international superstars, as the sport has attracted a vast global audience. In celebration of the 20th anniversary of UFC 1, we’ve decided to take a look back on some of the moments that have made the sport what it is today, with, The 50 Most Brutal MMA Matches of All Time.

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