Ranking the 20 Best WWE World Heavyweight Title Matches on Raw in the Past 20 Years

WWE World Title matches don’t happen on Monday Night Raw very often, so when we do get them they are usually quite memorable.

If we were lucky, getting to see a World Title match for free on television occurred maybe once a year on Raw, or before 1993, on Saturday Night’s Main Event. That all changed when WCW Nitro became competition for the WWE on Monday nights!  With each company forced to do whatever they could to win the ratings war, fans started seeing some great matches, some of which you'll learn about tomorrow. Considering the ratings war was going to determine which company would become the worldwide leader in pro-wrestling, you can imagine the stakes were high.

Televised World Championship title-switches also increased following the creation of the Money in the Bank. While not always the best matches, the MITB briefcase has frequently been cashed in on Monday Night Raw, leading to numerous iconic moments for the company.

Ranking these matches is a pretty tough task. In some cases the matches listed here might simply have been well-worked matches, or they might be on this list because of the impact they would have on the business of pro-wrestling and not so much because the match itself was anything special.

Since 1996 numerous World Championship Matches have taken place on Monday Night Raw, some of them good and some of them bad. Here are the top 20.

20 Roman Reigns vs. Sheamus w/ Vince McMahon as Ref January 4th 2016


The deck was stacked against champion Roman Reigns heading into his match with Sheamus in early 2016. Sheamus had cashed in the Money in the Bank briefcase at the Survivor Series to steal the title away from Sheamus, but Reigns then defeated Sheamus to win it back in late 2015.

Sheamus was granted his rematch on Monday Night Raw and just to ensure he snatched the championship away from Reigns, Vince McMahon (whom Reigns had punched a few weeks prior to this) was made the special guest referee.

Reigns would successfully defend the title after Vince got roughed up and a more objective referee ran down to count the 3.

19 Daniel Bryan vs. Triple H- April 7th 2014


The night after WrestleMania is always an important show, and the night after WrestleMania 30 was no different. The previous night Daniel Bryan defeated Triple H, and then won a 3-way match with Randy Orton and Batista to win the WWE Undisputed Championship.

The next night on Raw Triple H announced that Bryan would have to defend his title against Hunter himself. Bryan would win the match by DQ, but would have to fend off attacks from Triple H, Kane, Orton and Batista as the Authority looked to injure the guy who they didn’t want as “the face of the company”.

18 CM Punk Cashes in on Edge June 30th 2008


Edge was the first Money in the Bank match winner, perhaps fitting because he’s also the guy who came up with the idea. After winning the first MITB briefcase (and carrying it around for quite awhile) he finally cashed it in on John Cena, after Cena had just competed in an Elimination Chamber match.

Edge’s opportunistic approach to cashing in the MITB briefcase makes it hard to have any sympathy for what CM Punk did to him on June 30th 2008.

17 “Stone Cold” Steve Austin vs. Kane June 29th 1998


Possibly the hottest year in the history of the WWF was 1998, especially the period following Austin’s WWF Championship win at WrestleMania 14. Austin’s title reign took an un-expectant turn at the King of the Ring PPV however, as Kane won the title in a First Blood match with a little help from the Undertaker.

The next night on Monday Night Raw Austin demanded a rematch, and Kane (who was still not speaking by this point) nodded his head in approval and the rematch was on.

16 The Miz vs. John Morrison, Falls Count Anywhere : November 28th 2011

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John Morrison and the Miz had been intertwined for years by the time this match happened in 2011.

Miz and Morrison had been in ECW together when Morrison underwent his gimmick change from Johnny Nitro to a more Jim Morrison-inspired character. While they would initially feud with each other over the ECW Championship, they would quickly align and become a tag team.

After having a very successful run as a team they would go their separate ways, but after the Miz won the WWE Championship, Morrison was right there to challenge him.

15 The Miz vs. Jerry Lawler, TLC Match: November 29th 2010


Jerry Lawler challenged the Miz for the WWE Championship on his 61st birthday, and his request was granted by Monday Night Raw’s anonymous GM.

This all took place during a very dark period in the history of wrestling: the period when Michael Cole was a heel announcer.

While he actually played the role quite well, Cole’s heel commentary being heard consistently throughout a 3-hour wrestling program was just a bit too much.

The peak of Cole’s heat came during this match when he cost his broadcast partner a chance at winning the WWE Championship.

14 Bret Hart vs. Sid, Cage Match: March 17th 1997


Leading into WrestleMania 13 things were a little messy with the WWF title picture. Shawn Michaels had relinquished the title months earlier and  Austin, Bret Hart, the Undertaker and Sid were all in the running for it.

Austin was scheduled to face Hart, and Taker was scheduled against Sid in just six days at WrestleMania 13.

What ended up happening in this match is that rivals began helping rivals. Austin tried to help Hart win the title so that he could challenge him for it at WrestleMania, and Undertaker did the same in favor of Sid.

Sid (with Undertaker’s help) would retain the title, but lose it within a week to the Undertaker.

13 Austin vs. Ken Shamrock October 26th 1998

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Ken Shamrock created a name for himself in the early days of the UFC and came into the WWF in 1998 with a lot of buzz surrounding him.

Shamrock would make a few appearances leading into WrestleMania 13, where he refereed the submission match between Austin and Bret Hart and then began his in-ring career with the company shortly after that.

Later in 1998, Shamrock would join The Corporation in their efforts to get the title off of Austin. A title match was given to Shamrock on October 26th 1998 and just to ensure that Shamrock had an advantage, it was made a “Submissions” match.

12 RVD vs. Edge vs. Cena July 3rd 2006


RVD was the second ever Money in the Bank winner, and the second straight wrestler to successfully cash in and win the WWE Championship.

Instead of being opportunistic, RVD opted to name the date and place of his title opportunity ahead of time: The ECW One Night Stand PPV.

RVD defeated John Cena that night and became both the ECW Champion and the WWE Champion at the same time.

His title reign wouldn’t last long though. RVD and Sabu got pulled over and charged with having marijuana on them, definitely not a good thing! RVD was suspended and the decision was made for him to lose both World Titles.

11 CM Punk vs. JBL June 30th 2008


CM Punk had just shocked everyone by cashing in his MITB briefcase and winning his first ever World Championship. The cash-in seemed to come out of nowhere, especially back then when the concept of the MITB briefcase was still only a few years old.

After Punk successfully cashed-in on Edge, he was challenged to defend the title against JBL. The writing was on the wall for Punk to go down as a transitional champion, someone just given the belt briefly in order for it to be put on someone else shortly after, but we were wrong.

10 Seth Rollins vs. Neville August 3rd 2015


Seth Rollins had won the WWE Championship after cashing in the MITB briefcase at WrestleMania 31. By the end of that summer he was in the middle of a feud with John Cena.

Cena at this time was frequently defending the US Championship in an open-challenge format, so Rollins decided to do the same thing with his WWE Championship.

9 Rey Mysterio vs. John Cena July 25th 2011


Following the epic 2011 Money in the Bank PPV where CM Punk defeated John Cena for the WWE Championship, the title was declared vacant as Punk’s contract had expired and he was seemingly gone from the company.

Rey Mysterio defeated the Miz in the finals of the tournament, making it the first WWE Championship win for Mysterio (although he had been World Heavyweight Champion). He would be forced to defend the title later that night against former champ John Cena however, a match that Cena would win.

8 Kane vs. Triple Mask vs. Title June 23rd 2003


In 2003, Triple H offered Kane a spot in his faction “Evolution”. This may be shocking considering the pair had feuded for sometime, including during the infamous “Katie Vick” angle. Steve Austin (Who was the Co-General Manager of Raw at the time) gave Kane the option of facing Triple H for the World Title if he turned down the spot in Evolution. The other co-general manager of Raw, Eric Bischoff then added the stipulation that if Kane faced Triple H for the championship, Kane would have to put his mask on the line.

Kane chose to face Triple H for the World Title the next week on Raw from Madison Square Garden. Evolution would interfere in the title match, costing Kane both his mask and the World Title.

7 Roman Reigns vs. Sheamus December 15th 2015


The WWE has done everything it can think of to try and get Roman Reigns over as a top babyface. In late 2015 they decided to try and get Roman over by having him punch Vince McMahon in the face and win the World Title on the same night.

Reigns convinced Vince McMahon earlier in the night to give him a WWE Championship match against Sheamus, but McMahon added the stipulation that if Reigns didn’t win the title he would be fired.

6 Edge vs. Ric Flair TLC Match January 16th 2006


Edge is one of the most decorated champions in the history of the WWE, but Ric Flair is the most decorated World Champion of all time.

The two would meet on January 16th 2006 in Edge’s speciality: a Tables, Ladders, and Chair match.

Lita managed Edge at the time, and she would play a pivotal role in helping Edge retain his championship. This was also the first time the WWE Championship was ever defended in a TLC match.

Had Flair come out victorious, it would have been his 17th world championship, but he still holds the record with 16.

5 Alberto Del Rio vs. CM Punk November 28th 2011


The WWE Championship bounced around several times in 2011, with John Cena, Rey Mysterio, CM Punk and Alberto Del Rio all getting in on the fun.

After Punk defeated Cena in the main event of Summerslam, Del Rio cashed in his MITB briefcase and became the first ever Mexican born WWE Champion.

From there, he lost the title to Cena but regained it at the Hell in a Cell PPV in a match against Cena and Punk. He would lose the title to CM Punk at that year’s Survivor Series, but was granted a rematch on the November 28th Monday Night Raw.

4 Triple H vs. Chris Jericho April 17th 2000


The anticipation leading to Chris Jericho’s 1999 debut in the WWE was palpable. Jericho had more or less sat out the reaming dates of his contract with WCW, as the company was hesitant about putting him on TV due to the belief that he was jumping ship to the WWE shortly. So for several months before he would actually show up on WWE television, fans were awaiting his arrival.

When he finally did make it to the WWE in August of 1999, he had an iconic back and forth verbal sparring contest with the Rock and it looked like a new star had been born. But then not much at all happened with him; he feuded with mid-card guys over mid-card titles and got lost in the shuffle.

Then, in a possible attempt by the WWE to test how the audience would respond to him winning the championship, Jericho defeated Triple H for the World Title!..Only for the decision to be reversed shortly after.

3 Triple H vs. Shawn Michaels December 29th 2003


If you went to Monday Night Raw in San Antonio on December 29th 2003, you probably had a really good time.

In one of the best matches in the history of Monday Night Raw, Shawn Michaels and Triple H almost went 30 minutes on live TV for the WWE Championship.

Triple H was the champion heading into the match, with Shawn Michaels playing the role of the hometown hero. Michaels had recently returned to in-ring action after having been retired due to back injuries for more than 4 years.

The match was a back and forth affair with several near falls. It had looked as though Michaels had won the title in his hometown; only for stand-in referee Eric Bischoff to rule that both wrestlers shoulders were pinned to the mat at the time he counted 3 and that Triple H was still the champ.

2 Undertaker vs. Jeff Hardy Ladder Match


A lot of wrestling fans really like Jeff Hardy a lot, like a whole lot. Those fans were probably pretty happy when Jeff Hardy was given a WWF Championship Ladder match with the Undertaker on January 7th 2002.

While Taker would defeat Hardy, Jeff would continue to challenge the Undertaker after the bout was over, seemingly showing just how determined the young Hardy boy was. Jeff would earn Undertaker’s respect through this, and Taker would raise Hardy’s hand to close the segment.

After this match Jeff began wrestling in more singles matches, even winning the European title shortly afterwards.

1 Rock vs. Mankind


Mick Foley finally won the WWF Championship on December 29th 1998, although it was not broadcasted until January 4th 1999.

The title win for Mankind had huge implications as it concerned the Monday Night Wars. On the night that Mankind’s title win was to air, Tony Schiavone was instructed to announce to the WCW Nitro viewing audience that Foley was going to win the WWF title on Raw. The idea was that spoiling the main event of Raw would keep people watching Nitro, but just the opposite occurred. Fans turned over to Raw to watch the popular Mick Foley win the title, and tuned off WCW which aired the “Finger Poke of Doom” match between Hogan and Nash that night.

Raw won the battle for rating supremacy on that night, setting the tone for the rest of 1999 and WWE’s eventual victory in the Monday Night Wars.


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Ranking the 20 Best WWE World Heavyweight Title Matches on Raw in the Past 20 Years