Four big matches in Shelton Benjamin’s WWE run

Shelton Benjamin is a beloved figure in professional wrestling and his time in WWE featured several big moments. 

Shelton Benjamin is a legend in professional wrestling. His 20 years in the WWE cement him as one that deserves recognition. Many believe WWE missed out big time by not making him a champion during his initial run with the company, and it’s a huge hole that can’t be ignored. Still, Benjamin’s tenure in the company has several big moments and matches that can’t be ignored. This is a look back at four big matches in Shelton Benjamin’s time with the WWE.

2005 Money in the Bank Ladder Match

The Money in the Bank ladder match is a car crash of a wrestling spectacle. Since its inception, there have been hours of ridiculous highlights of wrestlers doing amazing feats when the spotlight shines the brightest. Shelton Benjamin is one of those individuals and his performances in the Money in the Bank ladder match were a must-see affair. Much like Kofi Kingston in the Royal Rumble, Benajamin was frequently added to the match to create some type of highlight, and he always delivered.

2005 was a big year for Benjamin, as other matches on this list will show, and this is perhaps the year he should have captured the briefcase. There was a moment when Jericho was at the top of the ladder himself, but Benjamin ran up another ladder to land a clothesline on the former AEW Champion, all without missing a step.

Shawn Michaels versus Shelton Benjamin – WWE Raw, May 2, 2005

In 2005, WWE put together a Gold Rush tournament where the winner would get a shot at the championship. The first-round matches were drawn at “random” setting the stage for some surprise pairings. Shawn Michaels versus Shelton Benjamin was such a surprise and it certainly delivered.

This was the match where Benjamin provided, he belonged. He was in the middle of his first run as a singles champion, holding the Intercontinental Championship. But this was the match that let the world know Benjamin had all the tools to be a main event talent. This is also the match that includes perhaps the best superkick of all time when Michaels caught Benjamin flying through the sky to get the 1-2-3.

Cedric Alexander & Shelton Benjamin versus The New Day (Kofi Kingston & Xavier Woods) – WWE Raw, November 16, 2020

This was a match for the fans. The Hurt Business and The New Day were two of the most over acts with fans and they represented a level of Black Excellence in professional wrestling that doesn’t get to shine at the top too often. The tag team titles were on the line and for 16 minutes these four men reminded the world why they were two of the best teams in the industry.

Later, that same year, The Hurt Business would take the title from The New Day on another edition of WWE Raw, but this is the match that stands out as among the top when looking at their catalog of matches.

Kurt Angle versus Shelton Benjamin – WWE Raw, August 22, 2005

Again, 2005 was a major year in Benjamin’s growth as an individual performer. He, along with Charlie Hass, came into the WWE as a part of Team Angle under the moniker of The World’s Greatest Tag Team. But after the faction split, it would be Benjamin who reached the higher of the two heights. One of those moments came against Kurt Angle on WWE Raw.

Of course, it was Angle who picked up the win, as we’re talking about a time in his career when he was the guy for WWE. But seeing Benjamin stand toe-to-toe with another icon of that time shows just how high he could have gone up the ladder.