The late 80s was a very time for American Wrestling. Many legends were in the best shape of their lives and going through the best period in their career.

Many young wrestlers were eager to climb the hierarchies and win world titles and veterans wanted to show everyone that they still have a lot to give.

This was also a time when one legend was at his peak. I was working on a list of the best matches of 1989 when one name just kept coming up, Rick Flair. So instead of looking at the year, we are going to look at the man. These are the

5 Best Flair Matches Of The Late 1980s

Ric Flair Vs Barry Windham – NWA Jim Crockett Memorial Cup (April 10th, 1987)

Both Flair and Windham were highly skilled and charismatic wrestlers, known for their technical abilities and captivating personalities. Flair, a multiple-time NWA World Heavyweight Champion, was the epitome of flamboyance and arrogance, while Windham, a talented second-generation wrestler, possessed a combination of strength and agility.

Their match at the Jim Crockett Memorial Cup was highly anticipated, The match was an intense back-and-forth affair, with both competitors showcasing their signature moves and countering each other’s attacks.

Flair’s cockiness and Windham’s determination added an extra layer of drama to the bout.

In the end, after a grueling battle, it was Ric Flair who emerged victorious, securing a hard-fought win over Barry Windham and solidifying his status as one of the greatest wrestlers of his era.

Ric Flair Vs. Ricky Steamboat – NWA Wrestle War (May 7th, 1989)

The decisive match of the trilogy. An hour of on the clocks and three judges who would have to decide the winner in case of a tie and two wrestlers eager to prove to the world who was the best.

A fantastic masterpiece with a surprising ending and a clear (but not clear) victory by Flair, who becomes a favorite of the crowds for the first time in almost 10 years.

Shortly after this, “The Dragon” returned briefly to WWF, in a slight gimmick change that had him literally spitting fire. Of course, he would later return to WCW where he found success in a tag team with Shane Douglas and then renewed his rivalry with Ric Flair (more on that later)

Ric Flair Vs. Ricky Steamboat – NWA Chi-Town Rumble (February 20th, 1989)

The trilogy (or rather, the three matches broadcast on TV, given that Flair and Steamboat faced hundreds of times in that period even in non-television matches) between Ric Flair and Ricky Steamboat represents without a doubt the highest point in the history of NWA and perhaps of American wrestling with regards to quality in the ring.

Ric Flair, reigning champion and now an icon of the NWA, is a phenomenon in the ring, amazing in interviews, charismatic, and a real rock star. A smart, resistant heel, difficult to beat for everyone, who always had an ace up his sleeve.

The challenger, Ricky “The Dragon” Steamboat, already the author of one of the best matches in WWF history at Wrestlemania 3, against Randy Savage.

Former WWF Intercontinental Champion, Steamboat was unable to become a WWF World Champion due to conflicts with Vince McMahon (furious because Steamboat had asked for time off to help his pregnant wife) and with Hulk Hogan (who was afraid that Steamboat would become more popular than he was). Retired from competition, he returned to challenge Ric Flair and finally win the world title.

Two very different characters: the playboy and the family man, one smart and the other correct and loyal, both united by a great passion: wrestling.

The match was a real technical masterpiece that managed to involve all the fans perfectly. Everyone wanted to see Steamboat win, but Flair had many supporters, and the controversial ending was a guarantee of revenge.

The first round went to Ricky Steamboat, who became world champion, but that was only the beginning.

If you love wrestling, you absolutely must see this match.

Ric Flair Vs. Ricky Steamboat – NWA Clash Of The Champions 6 (April 2nd, 1989)

The revenge of the battle of “Chi-Town Rumble” ended controversially. This time the match was a 2 of 3 falls, where you had to beat your opponent twice in an hour to demonstrate that you are superior.

Again, the match was a masterpiece. Flair won the first fall, forcing Steamboat to increase the pace of the challenge, and “The Dragon” won the second fall. The third was a whirlwind of emotions, both wrestlers touched the victory several times, but in the end, it was Steamboat who won, but still controversially, given that Ric Flair had one foot on the rope at the time of the decisive pinfall, a very short time before the time limit.

So there was still no clear winner of the battle, a third match was needed!

This match was broadcast on the same evening as Wrestlemania V, but for free. The show, however, did not get excellent ratings. The booker George Scott was blamed for the bad ratings, because he had decided not to advertise this match, fearing that people, knowing of the possibility of seeing the free match on TV, would not buy tickets to see that match during the NWA tours.

Ric Flair Vs. Terry Funk – I Quit Match – NWA Clash Of The Champions IX (November 15th, 1989)

Terry Funk, legend, ex-NWA champion, and second-generation wrestler, attacked Ric Flair at the end of the third match with Steamboat, challenging him for the world title. The match had been won by Flair, but the challenge was far from over.

The final match was an I Quit Match: to win, you had to force your opponent to say “I Quit” into the microphone. This was the only rule.

Flair proved he was perfectly capable of fighting a real fight with no holds barred against a veteran like Funk.

Zero blood, but a lot of violence and intensity, is a real manual of how to fight a violent match without blood.

Flair wins, making Funk scream “I Quit.” Terry, who will retire from competitions for some time, returns to fight for the next twenty years and become the ECW world champion in 1997.