#1. Scott Hall vs. The 1-2-3 Kid - RAW, May 17th, 1993

All the matches on RAW that have been mentioned in this article were great upsets. However, when talking about the greatest upset in the history of Monday Night RAW, look no further than May 17th, 1993, when the established Razor Ramon was defeated by The Kid.
At the time, The Kid was a young 21-year-old named Sean Waltman, who would later go by the name of X-Pac. He made his RAW debut on May 3rd as The Kamikaze Kid but was unsuccessful against Doink The Clown. He took on Scott Hall, who was already an established WWE Superstar.
While it looked like it would be a typical squash match to make Razor Ramon look good, The Kid shocked the wrestling world with one moonsault, pinning Ramon by fluke and scoring a huge upset on RAW. In doing so, he earned the nickname 1-2-3 Kid.
It's one of RAW's early iconic moments. While 1993 wasn't a great year for WWE programming by any means, 1-2-3 Kid's win over Razor Ramon remains the greatest upset in RAW history.