10 Of The Most Iconic WWE Matches Of All Time

With such a long and storied history, the WWE has naturally had its fair share of iconic matches. So many wrestlers have hit the mat to cries and shouts from the crowd, fallen off ladders, or plummeted from the tops of cages that narrowing iconic matches down to ten seems almost cruel.

However, if we listed every single match that was pivotal to the WWE’s development, we’d be writing forever, so we’ll restrain ourselves. Here are 10 of the most iconic WWE matches of all time (not in order of importance, of course!).

1. “Hacksaw” Jim Duggan wins the first Royal Rumble, 1988

As the first Royal Rumble in WWE history, 1988’s competition is a very special one indeed. Although “Hacksaw” Jim Duggan wasn’t the first to enter the ring – and he certainly wasn’t anyone’s favourite – he managed to emerge from the competition victorious nonetheless. Speaking to Betway casino about his WWE career, Duggan attributes his victory to remain in the corners of the ring, where other wrestlers wouldn’t target him for brawls. Sneaky!

2. The Montreal Screwjob, 1997

Infamous among wrestling fans for its unscripted drama, the Montreal Screwjob is a special event indeed. It took place at 1997’s Survivor Series event and saw the Heartbreak Kid, Shawn Michaels, taking on Bret “The Hitman” Hart. In the run-up to the match, backstage drama saw Hart defecting to the WCW, and as a result, WWE head honcho Vince McMahon called the match in favour of Michaels early, causing Hart to knock McMahon out backstage.

3. Brock Lesnar vs. Kurt Angle, 2003

When people talk about professional wrestling – with particular reference to the WWE – they often point out how it’s staged, and that means wrestlers can’t sustain real injuries. However, this was markedly not the case in 2003’s WrestleMania match between Brock Lesnar and Kurt Angle, in which both men gave it all they had. A series of real, honest injuries were sustained by both fighters, leading to a competition that nobody who witnessed it will forget anytime soon.

4. The Undertaker’s final match, 2020

There’s no denying that The Undertaker is a legendary wrestler. Since his career with the WWE began back in 1990, ‘Taker has taken part (no pun intended) in some incredible matches. His final match in 2020 wasn’t as climactic or exciting as many of his previous engagements have been, but as his last match, it was a fitting sendoff. He battled AJ Styles in a Boneyard match, in which the loser would be buried alive. Naturally, the Undertaker won, and he exited the ring to Metallica’s “Now That We’re Dead”.

5. 1-2-3 Kid takes on Razor Ramon, 1993

One of the most shocking upsets in WWF Monday Night Raw history happened in 1993 when the wrestler is then known as the 1-2-3 Kid took on legend Razor Ramon in the ring. 1-2-3 Kid was nothing but an upstart, with Ramon the clear favourite to win, but 1-2-3 Kid pulled out all the stops and used his speed and agility to run rings around Ramon, eventually claiming the victory for himself. The 1-2-3 Kid eventually changed his name to X-Pac, and a legend of the sport was born.

6. The first Money In The Bank match, 2005

It stands to reason that Money in the Bank would debut at WrestleMania because it involves fighting for the right to a championship battle against the reigning champ. The setup is thus: it’s a ladder match with a briefcase suspended above the ring, and whoever grabs the briefcase wins the right to cash in the championship match contract. The first match happened in 2005 and was created by pioneer Chris Jericho, who participated in the match alongside fellow legends like Edge and Christian.

7. Hulk Hogan vs Andre the Giant, 1987

At the time, Hogan’s battle against the massive Andre the Giant (who was huge both physically and in terms of fame) was billed as the “biggest main event” sports entertainment had offered up to that point. Hogan was defending his title against Andre, and the two men squared off in the ring, with Hogan losing out to Andre’s clearly superior strength and stamina. Eventually, Hogan psyched himself up and, astonishingly, body-slammed Andre with a scoop slam, using his leg drop pin move to achieve victory.

8. Bret Hart vs Stone Cold Steve Austin, 1997

When Bret Hart took on Stone Cold Steve Austin at WrestleMania XIII, Austin was a heel, while Hart represented the acceptable face of the WWE, a technical wrestler with real skill and Hollywood good looks. This 1997 match changed all that. While the fans began chanting for Hart, eventually, as the match progressed, they changed allegiances, cheering for Austin and booing whenever his fortunes faded. Hart’s heel turn in that match was spectacular, and the rest, for Austin at least, is history.

9. The Fabulous Moolah vs Wendi Richter, 1984

This is probably the single biggest title upset in WWE history. The Fabulous Moolah is a world-famous, celebrated wrestler, and she’d held her Women’s Championship title for many years when she battled Wendi Richter in 1984’s Brawl To End It All event. Richter, accompanied by Cyndi Lauper (yes, that one), promptly dethroned Moolah after more than ten years holding the title, winning it for herself and establishing herself as the WWE’s face of women’s wrestling.

10. Mankind vs. The Undertaker, 1998

Do the words “Hell in a Cell” mean anything to you? If they don’t, then you almost certainly haven’t watched Mankind’s match against The Undertaker at the 1998 King of the Ring event. This classic match was so brutal and so celebrated that it became a meme, with Mankind being thrown off the cell by Undertaker, continuing to battle the giant despite having a dislocated shoulder. This event made legends of Mankind and Undertaker if they weren’t legends already.