In the late 1980s, Ric Flair had firmly established himself as the best wrestler in the world. Flair won the NWA World Heavyweight Championship a record eight times before he ran into a young challenger. This challenger shook the Nature Boy to his core and later developed into his greatest rival. This man was none other than the Icon, Sting.

The tremendous rivalry between Ric Flair and Sting

Flair and Sting first clashed at NWA Clash of Champions in 1988. The legends wrestled to a 45-minute draw, which won the Wrestling Observer Newsletter‘s best match of 1988 award. No one had come this close to taking Flair’s title before, but Sting would have to wait a long time before getting another shot.

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Flair recruited the Icon into the famed stable ‘The Four Horsemen’. Sting rescued Flair from an attack by the Great Muta, which led to his recruitment.

Unfortunately for the Stinger, his run with the Horsemen was jeopardised after he won a round robin tournament to challenge for Flair’s NWA World Heavyweight Championship. He beat Flair himself in the finals of the tournament.

The Horsemen pressured Sting into dropping the No. 1 Contender’s status, but he remained adamant. This led to him being beaten down by the Horsemen and kicked out of the great stable. An unfortunate knee injury put Sting out of action, but he returned fresher than a daisy and set to win the title.

Sting beats Flair for the NWA Title

At the 1990 Great American Bash, Sting finally triumphed over the Nature Boy. The Icon reversed the Figure Four leg-lock into a small package for the three count. The crowd in the Royal Farms Arena in Maryland erupted as the referee called for the bell.

Flair and Sting’s rivalry would continue till the former regained his championship under the guise of the Black Scorpion. The Black Scorpion defeated the Icon for the title at a WCW live show [WCW acquired NWA in 1991]. Flair and Sting’s rivalry would be paused as the former went to WWE.

After losing a ‘Loser leaves WWE’ match against Mr. Perfect, Flair was back in WCW. In 1993, WCW’s biggest superstar was Sting, who thrived in the absence of the Nature Boy.

A rivalry renewed: WCW’s biggest star vs NWA’s biggest star

Ric Flair still held the WCW World Heavyweight Championship, which he hadn’t relinquished since moving to WWE. Sting held the WCW International World Heavyweight Championship, a title he won from Lex Luger. This led to a unification match between Sting and Flair at Clash of Champions 1994.

It was Ric Flair who triumphed and won the WCW International World Heavyweight Championship and the WCW World Heavyweight Title. However, their rivalry did not end there.

Flair and the Icon main evented the first WCW Nitro. They even clashed at WCW World War III in 1995. The Icon made the Nature Boy submit to the Scorpion Deathdrop and put on the best match on a night where Randy Savage outlasted sixty men to win the WCW World Heavyweight Title.

The end of Sting and Ric Flair’s feud

Flair and Sting would wrestle WCW Nitro’s last match, after which the Icon would take a hiatus from wrestling before going to TNA. Flair would return to the WWE and continue his historic career.

The last time the legends would meet would be in TNA. It was fitting that Flair wrestled the last match of his career against his greatest opponent. Some might call Ricky Steamboat his greatest opponent, some might even call Shawn Michaels his most iconic rival. But for the wrestling historians and genuine fans of Flair, Sting was, and will always remain, his greatest opponent.

WATCH: When Sting Punished Hulk Hogan After a Controversial Defeat at Starrcade 1997