The Greatest Matches in WCW History: Flair vs Steamboat and more

As the only promotion to truly compete with WWE in the late 20th century, World Championship Wrestling (WCW) remains a crucial and beloved part of pro wrestling history. Some of the biggest names in the sport passed through WCW, the promotion that officially began under that name in 1988, initially owned by Ted Turner.

We’ve already highlighted WCW’s legendary wrestlers like Ric Flair, Sting, Hulk Hogan, and Booker T, but what about the matches? Below, we dive into the iconic matches that defined WCW and still resonate with fans and critics today.

Ric Flair vs. Terry Funk – Great American Bash 1989

Ric Flair and Terry Funk are two titans of wrestling, and their 1989 feud gave us some of the best matches in WCW history. At the Great American Bash, Flair defended the NWA World Heavyweight Championship against Funk in a hard-hitting battle that showcased Flair’s versatility as a babyface. Though Flair is often more associated with his heel work, this match stands as one of his finest in-ring performances, solidifying 1989 as perhaps the greatest year of his career.

Sting’s Squadron vs. Dangerous Alliance (WarGames) – WrestleWar 1992

WarGames matches in WCW were often hit-or-miss, but the 1992 showdown between Sting’s Squadron and the Dangerous Alliance was an undeniable hit. Featuring a stacked roster—Sting, Steve Austin (before he was Stone Cold), Ricky Steamboat, Rick Rude, and more—this match is remembered as one of the greatest WarGames bouts ever. It’s an explosive two-ring, steel cage brawl that perfectly captures the intensity and spectacle WCW brought to the table.

Ric Flair vs. Terry Funk – Clash of the Champions IX (I Quit Match)

Returning to Flair and Funk, their epic 1989 feud culminated in an “I Quit” match at Clash of the Champions IX. This was no ordinary TV event; WCW’s Clash shows delivered pay-per-view quality action for free, and this match was no exception. The intensity and emotion on display brought a fitting conclusion to one of wrestling’s greatest rivalries, proving that Flair and Funk’s chemistry could elevate any card to legendary status.

Eddie Guerrero vs. Rey Mysterio – Halloween Havoc 1997

The Cruiserweight division consistently stole the show in WCW, and the mask vs. title match between Eddie Guerrero and Rey Mysterio at Halloween Havoc 1997 was a masterclass in high-flying, fast-paced wrestling. Guerrero spent much of the match trying to unmask Mysterio, but Mysterio’s quickness and innovation kept him one step ahead. The match ended with Mysterio reversing a hurricanrana into a pin, securing his victory and cementing this bout as one of the greatest Cruiserweight matches of all time.

Ricky Steamboat vs. Ric Flair – Clash of the Champions VI (2-out-of-3 Falls)

One of the greatest trilogies in wrestling history is undoubtedly Ric Flair vs. Ricky Steamboat in 1989. Their 2-out-of-3 falls match at Clash of the Champions VI showcased the endurance and technical brilliance of both men. Running nearly an hour, this bout was an epic for its time, offering free TV audiences a match worthy of any pay-per-view. Though often regarded as the “worst” of their trilogy, it’s still an all-time great, illustrating how high the bar was set by these two legends.

Ricky Steamboat vs. Ric Flair – WrestleWar 1989

The third and final match of Flair and Steamboat’s 1989 trilogy took place at WrestleWar, where Flair regained the NWA World Heavyweight Championship. Though it wasn’t their best outing, it was still a stunning example of in-ring storytelling. The aftermath was equally memorable, as Terry Funk attacked Flair after the match, setting the stage for another iconic feud. WrestleWar 1989 is a standout in WCW history, bringing a close to one of wrestling’s most celebrated rivalries.

Ric Flair vs. Ricky Steamboat – Chi-Town Rumble 1989

The first match in the Flair-Steamboat trilogy at Chi-Town Rumble is considered by many to be the pinnacle of professional wrestling. If we were ranking the greatest matches in the history of the sport, this one could easily top the list. The pacing, the in-ring storytelling, and the pure athleticism on display were revolutionary. What makes this match even more impressive is that much of it was called on the fly, showcasing the incredible chemistry and skill of both men. Chi-Town Rumble remains a must-watch for any wrestling fan.

These matches represent the peak of WCW, a promotion that pushed the boundaries of professional wrestling during its heyday. From high-flying Cruiserweight action to grueling heavyweight rivalries, WCW’s legacy is cemented in these unforgettable moments.

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