general | March 27, 2026

Ranking Ric Flair's 10 Best Matches From This Era, Ranked

Ric Flair returned to WWE in November 2001 and was an integral part of the Ruthless Aggression Era. The two-time WWE Hall of Famer had a stellar career that spanned many decades and is widely regarded as the greatest of all-time in terms of his all-around in-ring work and skills on the mic.

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Flair lost his confidence due to his stint in WCW but once he mixed up with the very best from 2002 onwards in WWE, he was back to producing some of his finest matches in his career. Naitch is not The Dirtiest Player in the Game for nothing, he has built a reputation that many have tried and failed to emulate but left a lasting legacy with memorable matches.

10 Ric Flair Vs. Kenny Dykstra (New Year's Revolution 2007)

Ric Flair v Kenny Dykstra New Year's Revolution 2007 Cropped

Ric Flair began feuding with Kenny Dykstra, formerly of The Spirit Squad in late 2006-early 2007. Dykstra was embarrassed at Survivor Series when Naitch and his crew of legends defeated The Spirit Squad.

Hellbent on revenge, Kenny scored a few victories over Flair on Raw, and the two collided once more at New Year's Revolution 2007. This is an underrated clash and Flair encapsulates how good he is by putting on a magnificent match with younger talent. Ultimately, Naitch was unable to stop his losing run against Kenny, who scored another confidence-boosting win over the 16-time world champion.

9 Evolution Vs. Rock N' Sock Connection (WrestleMania XX)

Evolution v Rock n Sock

Evolution made Mick Foley's life a living hell with numerous beatdowns on Raw but it's not in Foley's DNA to stay down. Foley had a trick up his sleeve by calling on The Rock to be his partner at WrestleMania XX to take on Flair, Batista, and the Intercontinental Champion Randy Orton representing Evolution in a three-on-two handicap match.

Foley had his hometown fans giving him support with WrestleMania XX emanating at Madison Square Garden. This was an enticing contest with all five men playing their part to make this bout memorable. Nonetheless, the Legend Killer had the final word by nailing Foley with an RKO to earn a hard-fought win for Evolution.

8 Ric Flair Vs. Chris Jericho (SummerSlam 2002)

Flair v Jericho

Another underrated gem at SummerSlam 2002 pitted Ric Flair against Chris Jericho. Jericho, formerly the Undisputed WWF Champion, wanted to add the Nature Boy to the list of big names that he has beaten in his sublime WWE career.

The two had tremendous in-ring chemistry together, and Flair once again continued to build momentum in his full comeback year in WWE. However, Y2J insisted that Flair submitted to the Figure-Four Leglock, but he did not. Nonetheless, Flair applied his excruciating hold to Y2J and forced Jericho to tap out for his first victory at SummerSlam.

7 Ric Flair Vs. Randy Orton (Taboo Tuesday 2004)

Flair v Orton

Surprisingly, Ric Flair and Randy Orton closed out Taboo Tuesday 2004 instead of Triple H's World Heavyweight Championship bout with Shawn Michaels. Flair joined in the assault from Triple H and Batista when they unceremoniously booted Orton out of Evolution after he captured his first World Heavyweight Championship at SummerSlam.

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An overwhelming 68% of the vote was in favor of Flair and Orton's match at Taboo Tuesday to be a Steel Cage match. Flair quickly busted Orton wide open in the early stages of this encounter. Orton retaliated by throwing Naitch into the steel mesh which caused Flair to bleed. The Legend Killer won this captivating clash with the fans on his side by planting Flair with his patented RKO. After the match, the two had mutual respect by Flair extending his hand to Orton with Orton accepting the offer.

6 Ric Flair Vs. Mick Foley (SummerSlam 2006)

Flair v Foley

There were no secrets that Ric Flair and Mick Foley had a personal dislike for each other as Naitch criticized Foley's style of wrestling. Nonetheless, they remained professional and had a brutal I Quit match at SummerSlam 2006.

Neither man pulled any punches which made this encounter a violent affair. However, Flair gained the upper hand and beat The Hardcore Legend to a bloody pulp. Foley struck up an unlikely friendship with Melina, who came down to ringside to rescue Foley. Despite Melina's advances, Flair rebuffed Melina throwing in the towel. He was going to strike her with a barbed wire baseball bat which left Foley no choice but to utter the words "I Quit."

5 Ric Flair Vs. Eddie Guerrero (King Of The Ring 2002)

Flair v Eddie

Mr. McMahon regained sole ownership of WWE in June 2002 which led to Flair no longer being an authority figure. Therefore, Naitch found himself as an active in-ring performer once more and collided with Eddie Guerrero at King of the Ring.

Flair and Guerrero were no strangers to each other as they were familiar from their clashes in WCW. Eddie was motivated in his comeback year and he continued to have outstanding matches. This one is often forgotten but Chris Benoit's interference was thwarted by Bubba Ray Dudley. Nevertheless, Flair picked up a huge win over Guerrero in a match that is definitely worth rewatching on the WWE Network.

4 Ric Flair Vs. Triple H (Taboo Tuesday 2005)

Flair v Triple H

Triple H did the unthinkable by betraying Ric Flair on Raw Homecoming in October 2005. The two had been inseparable for three years, and that signaled the official ending of Evolution.

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Flair was the reigning Intercontinental Champion but the Game did not care one bit about the Intercontinental Championship as he wanted to inflict punishment on Naitch. The title was an afterthought in this feud but Flair pleaded for fans to put him in a steel cage match with Triple H at Taboo Tuesday. The result was slightly predictable as the title was at stake but it did not take anything away from this being an enthralling contest. Flair retained the Intercontinental Title by escaping through the cage door after laying the Game out with three brutal chair shots.

3 Ric Flair Vs. Edge (Raw, January 16, 2006)

Flair v Edge

The Rated-R era was in full swing when Edge cashed in his Money in the Bank briefcase on John Cena at New Year's Revolution 2006 to become the WWE Champion for the first time. Edge was embroiled in a rivalry with Ric Flair, who interrupted his Live Sex celebration with Lita.

However, on the January 16th, 2006, edition of Raw, Edge defended the WWE Championship against Flair in a TLC match. Flair is not a TLC match specialist by any stretch of the imagination, but he put on a remarkable performance against Edge. He pushed the reigning champion to the limit with the two fighting blow-for-blow at the top of the ladder. Edge nailed Flair harder which caused Flair to fall with the Rated-R Superstar retrieving the title.

2 Ric Flair Vs. Triple H (Survivor Series 2005)

Flair v Triple H

Flair retained the Intercontinental Title against Triple H in a brutal Steel Cage match at Taboo Tuesday 2005. However, the problems were far bigger than the Intercontinental Championship. The two former best friends culminated their rivalry in a Last Man Standing match at Survivor Series.

The Cerebral Assassin relied on his old faithful, the Sledgehammer, to keep Flair down who proved that he could hang with Triple H every step of the way by getting up from three Pedigrees. A sickening Sledgehammer shot to the back kept the Nature Boy down.

1 Ric Flair Vs. Shawn Michaels (WrestleMania XXIV)

Flair v Michaels

Ric Flair's retirement match at WrestleMania XXIV was one of the most emotional matches in WWE history. Naitch competed against Mr. WrestleMania, Shawn Michaels, who had a tremendous amount of respect for Flair.

The two told a compelling story that captivated the audience, who were hoping to see Flair continue his career. However, Michaels put the Nature Boy out of his misery with a Sweet Chin Music. An emotional Flair hugged his children including Charlotte at ringside as Flair rode into the sunset with his integrity intact.

NEXT: Shawn Michaels' 10 Biggest Wins In His Career