Top 20 Favorite Matches of the 2000s

This list is purposely spoiler free because I want you to enjoy these matches like I did, fresh and surprising!

20.)  Rob Van Dam Vs. John Cena (c)

WWE Champion ship Match at ECW One Night Stand 2006

John Cena 

To say that John Cena was disliked by the ECW audience would be a great understatement. For example, the crowd rabidly chanted “F*** You, Cena!” on a near continuous loop throughout the match. One person had a sign that said, “If Cena Wins, We Riot.” On the contrary, Rob Van Dam was over like rover. The popular Van Dam was the crowd favorite because he was of his strong ECW roots. For pure passion, this crowd was unparalleled.

19.)  Hulk Hogan Vs. The Rock

Wrestlemania 18 (2002)


This match was the definition of a dream match because this contest contained two of the three most iconic WWE superstars in history. The Rock was still in his prime, but Hulk Hogan was well past his best days. Toronto, ever the fan of the heel, showed why Canadian wrestling fans live in “Bizarro World.” This especially true when they decided to cheer the vicious heel, Hogan. Some fans will remember that on the previous month’s Raw, Hogan attempted to murder The Rock with a diesel truck.

18.)  Shane McMahon Vs. Kurt Angle

Street Fight Match at King of the Ring 2001

Shane McMahon is a crazy man. His opponent, Kurt Angle tried to belly to belly suplex McMahon through a glass stage, but it did not break, Shane’s head bounced off the floor at least three times during the match. Ever the show man, Shane still wanted to keep the match going as planned. McMahon demanded that Angle throw him through the glass. McMahon and Angle aimed to satisfy the crowd with athleticism and violence, and they accomplished that goal.

17.)  Randy Orton Vs. Mick Foley

Hardcore Match at WWE Backlash 2004

Randy Orton proved his toughness in this match. Early on, Mick Foley took the fight to Orton by bringing his bag of tricks, including his barbed-wired 2×4 and thumbtacks. The look on Randy Orton’s bloodied and battered face told the story of how much sudden pain he felt as he was slammed onto the thumbtacks. The “Legend Killer,” Randy Orton had the drive to fight back against Foley even after the punishment that he endured.

16.)  Chris Benoit (c) Vs. Chris Jericho

Ladder Match for the WWF Intercontinental Title at Royal Rumble 2001

Chris Jericho Benoit

This ladder match had many innovative spots, on such spot was when Jericho put the Walls of Jericho onto Benoit at the top of the ladder. There was plenty of violence found in this match, including the use of steel chairs, but it was well-paced as you would expect from these two great wrestlers.

15.)  Royal Rumble Match (2001)


Kane was the standout star in this Royal Rumble match and it was one of the most entertaining Royal Rumbles of all time. The Big Red Machine laid waste to eleven other participants as he eliminated them by throwing them over the top rope; it looked pretty amusing to see huge men fly over the ring. Additionally, this match is one of the few Rumble matches that allowed weapons, weapons that the hardcore wrestler used to cause carnage. Stone Cold, Undertaker, and The Rock  brought the star power, and Drew Carey’s cameo as a participant in the match was comedic fun.

14.)  Chris Benoit and Kurt Angle Vs. Rey Mysterio and Edge

Tournament Finals for WWE Smackdown Tag Team Titles at No Mercy 2002

By booking four insanely talented wrestlers in a tag team match, the WWE guaranteed an amazing match, anything less would have been a huge disappointment. This match was the tournament finals to crown the inaugural Smackdown Tag Team Champions. The big question going into the match, how on earth would Benoit and Angle get along after all of the battles they had endured with each other? If you have time, check out this action-packed tag match if you’ve never seen it, and after twenty-two glorious minutes, you will thank me.

13.)  Mick Foley Vs. Edge

Hardcore Match at Wrestlemania 22 (2006)

Foley Edge

Prior to this match, Edge constantly made fun of Foley for never having a “Wrestlemania moment” in his long career. Edge felt that Foley didn’t have the drive to be his old self anymore, and Foley set out to prove Edge wrong. This hardcore match was good fun, but definitely not for the faint of heart.

12.)  John Cena Vs. Shawn Michaels

Raw April 23, 2007

A large, vocal portion of the audience felt that John Cena could not wrestle out of a wet paper bag. However, this match proved some of these doubters wrong. Previously, Cena and Michaels main-evented Wrestlemania 23. That match was good, this match was better. This episode of Raw was in the United Kingdom, and the audience was treated to an unexpected, nearly hour long match, in which John Cena held his own against the great Shawn Michaels.


Michaels Cena

11.)  Kurt Angle (c) Vs. Chris Benoit

WWE Championship Match at Royal Rumble 2003

Angle Benoit

Immediately prior to this WWE Championship match, there was an all-time dud of a World Heavyweight Championship match between Triple H and Scott Steiner, largely because Steiner was gassed a few minutes into that match. In contrast, Benoit had an amazing match and received a standing ovation courtesy of his great performance. There will never be such a stark difference between two matches again, Steiner’s dud and Benoit’s masterpiece.

10.)  Kurt Angle (c) Vs. The Undertaker

WWE World Heavyweight Title Match at No Way 2006

Angle Undertaker

By being a wrestling machine, Kurt Angle believably went toe-to-toe with The Undertaker. In this match, Angle was a pit-bull that viciously attacked Undertaker’s leg, and it was hard to imagine either man losing. Ultimately, the winner of this match would defend the championship against Randy Orton at Wrestlemania 22.

9.)  Stone Cold Steve Austin Vs. Triple H

Three Stages of Hell of Match at WWE No Way Out 2001

Austin HHH

The first ever, “Three Stages of Hell Match,” is also the best. The matches were in the following order:  singles match, street fight, and cage match. This match culminated of a bitter rivalry between Austin and Triple H, when it was discovered that Triple H hired Rikishi to run over Austin with a car in the parking lot earlier in the evening. This match was full of high-energy, fun violence, steel chairs, a sledge hammer, and a 2×4 wrapped in barbed wire. Even though one man had to lose, both wrestlers emerged from this match with their tough guy credibility intact.

8.)  Shawn Michaels Vs. Triple H

Unsanctioned Match at WWE Summerslam 2002

Michaels HHH

After Shawn Michael’s back injury in 1998, it appeared that his career was finished, but Michaels decided to do this one-of match against Triple H. Since this match was so well-received, “The Heart-Break Kid” decided to stay with the WWE until 2010. Previously, Triple H repeatedly attacked Michaels on Raw and provided some much needed context and hatred to this match.

7.)  Shawn Michaels Vs. Kurt Angle

Wrestlemania 21 (2005)

This is Kurt Angle’s best match of all time, which shouldn’t be a huge surprise. Angle and Michaels are among the best to have ever laced up wrestling boots so this match was highly anticipated by the fans. The build up was an inter-promotional match, Michaels represented Raw and Angle represented Smackdown. To provide some context for this match, Angle brought back some of Michaels’ old companions to WWE, including Sherri Martel and Marty Jannetty. Angle broke Jannetty’s ankle to get in the head of Michaels and sang a parody of Michaels’ theme with Martel, called “Sexy Kurt.” When the match started, the fun and games were over and these two put on a wrestling clinic.

6.)  Triple H (c) Vs. Cactus Jack

Street Fight Match for the WWF Championship at Royal Rumble 2000

Cactus Jack HHH

Mick Foley was the master at elevating talent to the main-event scene, if a wrestler matched his intensity and craziness, then they would probably make it on the main roster. Earlier on in this list, I noted that Foley wrestled and helped the careers of Orton and Edge. In this instance, Foley helped another Triple H become a credible force on the WWE main roster. Prior to this match, plenty of fans had a hard time buying into Triple H as a legit main-eventer. In a surprising twist, Triple H turned violent in this match, and it led to him becoming the “Cerebral Assassin.”

5.)  The Dudley Boyz (c) Vs. The Hardy Boyz Vs. Edge and Christian

TLC Match for the WWF Tag Team Championships at Wrestlemania 17 (2001)

Hardy Edge

If you are a fan of over the top violence, then this is the match for you. Table, ladders, and chairs were used constant basis. Even though some jaded fans would call this match a “spot-fest,” this match was pure fun. The highlight of the match was when Jeff Hardy dangled over the center of the ring while holding onto the tag team titles. As he descended the ladder, Edge speared him; Hardy, looking like a rag doll, spectacularly smashed to the floor. Ultimately, this match was the show-stealer, and the Astrodome crowd showered the wrestlers with cheers.

4.)  The Rock (c) Vs. Stone Cold Steve Austin

No Disqualification Match for the WWF Championship at Wrestlemania 17 (2001)

Austin Rock

The kings of the “Attitude Era” squared off at the height of their powers and popularity. This was the kind of match where you couldn’t picture either wrestler taking the pinfall. Both performers were very popular with the crowd going into the match, although Austin was slightly favored because Wrestlemania 17 took place in his home-state of Texas. Austin won the Royal Rumble that year, and The Rock beat Kurt Angle for the WWF Championship to set up this match. This match was full of violence and drama with plenty of false-finishes. In a bittersweet turn of events, this match probably marked the end of the “Attitude Era.”

3.)  Triple H (c) Vs. Shawn Michaels Vs. Chris Benoit

WWE World Heavyweight Title Match at Wrestlemania 20 (2004)

This is Triple H’s best match and it is the best Triple-Threat Match in WWE history. The Madison Square Garden crowd definitely appreciated this main event contest, with all three wrestlers working hard to be the best wrestler on the planet. The ending sequence was phenomenal and the after-math was highly emotional. A small disclaimer for this match, the after-math was certainly emotional and a bit surreal considering what we now know about Benoit and the surprise guest.

2.)  Christopher Daniels (c) Vs. AJ Styles Vs. Samoa Joe

TNA X-Division Title Match at Unbreakable 2005

This is by far the best TNA match of all time. Although the wrestlers maintained a frantic pace throughout the entire match, they never lost control.  The sequences to this contest were highly creative, violent, athletic, and entertaining. People enjoy A.J. Styles and Samoa Joe currently, but they were extremely talented before they made the main roster, and this TNA match is proof positive of their excellence. Finally, Christopher Daniel more than held his own in this contest.

1.)  The Undertaker Vs. Shawn Michaels

Wrestlemania 25 (2009)

Undertaker Michaels

This match is magical because in one corner you have the greatest Wrestlemania performer of all time, Shawn Michaels, going against the man who never lost at Wrestlemania, The Undertaker. Jim Ross was the play by play announcer for this match and did some of his finest work, which heightened the drama, with calls such as, “I think I just had an out of body experience!” Everything about this match was perfect, complete with the facial expressions of the wrestlers, the work in the ring, and the undeniable drama.