4 oldest WWE King of the Ring winners of all-time

WWE will continue its effort to expand the company's product beyond the U.S. borders as the promotion travels to Saudi Arabia for another premium live event - King and Queen of the Ring. This won't be the first time Jeddah hosts a major event, as last year the company brought the Night of Champions event to the Jeddah Super Dome, and in 2022, Elimination Chamber was also held in the city.

The company introduced King of the Ring in 1985 when WWE was exploding into the mainstream. With the popularity of wrestling being at an all-time high, earning the title of King was an incredible honor. Today, we take a look at some of the more seasoned vets who have held the crown. This is our list of the oldest King of the Ring winners of all time.

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#5. 1989 King of the Ring Tito Santana: 36 years old

Tito Santana won the crown in 1989!

In 1989, the likes of Ric Flair and Hulk Hogan dominated the professional wrestling world. Hogan was not only the face of the WWF, but Hulkamania was 'runnin wild all over the world. With that said, WWE had a pretty solid roster of top-level stars, one of which was Tito Santana.

Fans in Rhode Island enjoyed quite the treat in October 1989. WWE held the King of the Ring Tournament in Providence, in what was a non-televised event that featured 15 bouts, ultimately ending with Tito Santana winning the tournament. He ran quite the gauntlet, which started with Bad News Brown in the first round and finished with Santana defeating 'The Model' Rick Martel in the finals.

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#4. 2008 King of the Ring William Regal: 39 years old

King William Regal addresses the WWE Universe from his throne!

Despite professional wrestling being incredibly popular at the moment, some would argue that the industry has gone away from the typical roughnecked brawlers and larger-than-life personas that we once watched. William Regal was certainly one of the old-school hard-nosed brutes.

On April 21, 2008, WWE held a special episode of RAW, centered around the King of the Ring tournament. William Regal was 39 then and not the odds-on favorite to win the crown. However, after making quick work of Hornswoggle in the quarter-final round, he then defeated Finlay in the semi-finals and capped off the night by catching CM Punk with a Regal Stretch, causing Punk to submit.

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#3. 2006 WWE King of the Ring Booker T: 41 years old

2006 brought the era of King Bookah'!

Booker T is known as one of the greatest all-around stars in pro wrestling history. He was successful as a tag team wrestler with Harlem Heat and then went on to enjoy a great singles run. In mid-2006, WWE held the King of the Ring tournament between April 14th and May 21st.

The final round took place at the Judgment Day pay-per-view, with Booker T beating Bobby Lashley to become the 2006 King of the Ring.

Booker T's King of the Ring win evolved into a storyline involving several other WWE Superstars joining King Booker's Court. Hornswoggle, Sharmell, Finlay, and William Regal served as Bookers' underlings. With the help of King Booker's Court, Booker T went on to capture the World Heavyweight Championship at the Great American Bash.

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#1. 1986 WWE King of the Ring Harley Race: 43 years old

King Harley Race addresses his peasants.

Many wrestling fans consider Harley Race to be one of, if not the greatest of all time. Harley is one of the most important figures to contribute to the massive success of the glorious territory era. During his time under the National Wrestling Alliance umbrella, Harley held the coveted "10 pounds of gold" 8 times, with a total of 1,800 days as the NWA Worlds Heavyweight Champion.

Harley Race made the jump from the territories to the WWF in 1986. Shortly after signing with the company, Race entered the King of the Ring Tournament as he looked to cement himself as one of the top stars in the WWF. The tournament was stacked with some legendary stars from that time. Harley defeated Pedro Morales in the final round, becoming the oldest person to win the King of the Ring at 43 years old.

After winning the 1986 King of the Ring crown, Harley Race turned his win into a storyline where his opponents were often forced to bow in his presence. At WrestleMania 3, Harley defeated Junkyard Dog in a "loser must bow" match.

Harley retired in 1990, ending a legendary career that spanned over 3 decades. He is one of only a few wrestlers to be inducted into the WWE, NWA, and WCW Halls of Fame.