10 Greatest WWE Matches Of The 2000s

Triple H vs Cactus Jack WWE 2000s

The 2000s was the most newsworthy decade in wrestling history. It saw the demise of WCW and ECW, the second and third largest wrestling promotion of the 1990s as well as the birth of TNA (now Impact Wrestling) and Ring of Honor.

For WWE it heralded the end of the Attitude Era, which had yielded their greatest ratings and creative success. However, for fans, it is remembered as a decade of phenomenal in-ring competition which gave us numerous classic matches. This feature looks back on the 10 finest matches of the 2000s.

#10 TLC II – WrestleMania X-7 (April 1, 2001)


WrestleMania X-7 is renowned as one of, if not the greatest WrestleMania of all time. It’s certainly the best of the 2000s.

It holds that reputation as it took place at the peak of the company’s hottest-ever period and also played host to a number of all-time classic bouts. Two of which feature on this list.

The first is TLC II, which saw defending Tag Team Champions, The Dudley Boyz battle The Hardy Boyz and Edge and Christian in a rematch from their classic TLC collision at SummerSlam 2000.

The sequel improved upon the original as the key spots were bigger, there was outside interference from Lita, Spike Dudley, and Rhyno as well as non-stop thrilling action.

One of the best stunt-filled matches ever and more than two decades on still retains its power. A true classic.

#9 Kurt Angle vs Chris Benoit – Royal Rumble (January 19, 2003)

Chris Benoit vs Kurt Angle

For obvious reasons, Kurt Angle versus Chris Benoit for the WWE Championship at the 2003 Royal Rumble is rarely mentioned in 2023. However, at the time and for a few years afterwards, Angle versus Benoit was renowned as the greatest match in the history of the Royal Rumble and one of the best WWE Title matches ever.

It was impossible for ‘The Olympic Hero’ and ‘The Rabid Wolverine’ to have a bad match and the pair utilised fluid chain wrestling to thrill the live crowd in Boston. The match built slowly and built to an incredible crescendo down the stretch with a massive amount of false finishes.

This is undoubtedly one of the finest technical wrestling matches of all time and warrants its spot as one of the best matches of the 2000s.

Benoit’s involvement will permanently sully the match’s memory. However, judged on its own merits, the contest remains one of the best WWE matches of all time.

#8 The Rock vs Stone Cold Steve Austin – WrestleMania X-7 (April 1, 2001)

Rock vs Austin 2000s

The second WrestleMania X-7 classic was the headliner between WWF Champion, The Rock and Stone Cold Steve Austin, which heralded the peak and the conclusion to the ‘Attitude Era.’

Fought under No DQ rules, the match escalated into an intense brawl that had the Texas crowd hooked for every second.

The story of the contest was Austin’s willingness to go to any lengths necessary to win the gold and his growing frustration when The Rock kicked out of everything the ‘Rattlesnake’ could throw at him.

Enter Stone Cold’s arch nemesis, WWF Chairman, Vince McMahon, who shockingly aligned with his long-time enemy and screwed The Rock out of the WWF Championship.

A new era had dawned and the WWF would never be the same again.

#7 Triple H vs Chris Jericho – Fully Loaded (July 23, 2000)

Triple H vs Chris Jericho 2000s

Fully Loaded 2000 lived up to its moniker. The card was stacked with big-time matches, including a Triple Main Event. One of those bouts was the Last Man Standing war between Triple H and Chris Jericho.

The pair had been at odds ever since Jericho had upset “The Game” for the WWF Title, only to be denied when Triple H forced referee, Earl Hebner to overrule his own decision.

The psychology was sound as Triple H targeted Jericho’s ribs and Y2J sold like he had been mauled by a lion. Triple H dominated the bout but Jericho timed his sporadic comebacks perfectly and at times looked as if he may upset ‘The Cerebral Assassin.’

The finish came when Triple H back-suplexed Jericho through the announce table. With both men spent, Triple H managed to (briefly) rouse himself at the count of nine to win the bout.

This match had everything; lashings of claret, perfect storytelling, terrific action, and full-on brawling. A truly terrific contest.

#6 Randy Orton vs Mick Foley – Backlash (April 18, 2004)

Randy Orton vs Mick Foley

‘The Legend Killer’ punted Mick Foley down a flight of stairs on a memorable episode of Raw in June 2003, which (eventually) led to a vengeful Foley returning in the 2004 Royal Rumble match and seeking revenge.

After clashing in a tag team bout at WrestleMania XX, the ante was upped weeks later at Backlash, as Foley clashed with Orton in a Hardcore bout with the Intercontinental Title at stake. ‘The Hardcore Legend’ introduced a barbed wire bat early and tore strips out of Orton’s face.

Orton’s comeback was halted when Foley reversed an RKO attempt and sent him flying into thumbtacks. The finish came when Orton nailed the RKO on the barbed wire bat.

Brutal and incredibly violent with an excellent story. This was a big-time match that delivered in spades. It solidified Orton as the next major star and four months later he would become the youngest World Champion in WWE history.

#5 Shawn Michaels vs Chris Jericho – No Mercy (October 5, 2008)

Shawn Michaels vs Chris Jericho

Shawn Michaels was the MVP of the 2000s. From his 2002 comeback through to his 2010 retirement, no one had more classic bouts than ‘The Showstopper’. This is his first of four appearances on this list.

Michaels and Chris Jericho feuded for most of 2008 and clashed four times on pay-per-view that year. All of their collisions were excellent but their Ladder Match war over the World Heavyweight Title was the best of the bunch.

The match began slowly as each man felt each other out in some high-quality exchanges, before ramping up when the ladder was brought into play. In a nice callback to their previous encounters, Jericho targeted Michaels’s injured eye. In response, Michaels worked over Jericho’s leg after he got it caught in the ladder.

The pair utilised the ladder for several innovative and high-impact spots before they both simultaneously pulled the belt down together. They engaged in a tug of war before Michaels pulled Jericho towards him, which accidentally caused Y2J to headbutt him. Michaels fell and Jericho held onto the strap to win the bout and retain the gold.

Logical storytelling and high-impact spots mixed in with an intense feud contributed to one of the finest Ladder Matches in WWE history. An instant classic.

#4 Triple H vs Cactus Jack – Royal Rumble (January 23, 2000)

Triple H vs Cactus Jack

Triple H’s feud with Mankind was dialled up to 11 when Mankind transmuted into Cactus Jack to set up their Royal Rumble bout for the WWF Championship. ‘The Game’ started the bout by working over his foe before Cactus introduced weapons into the match, swinging the contest in his favour.

A barbed wire bat made a right mess of Triple H’s face and his leg was badly cut open when he was suplexed onto a wooden palette. The back-and-forth action culminated when Triple H nailed the Pedigree onto thumbtacks. A three count later and ‘The Cerebral Assassin’ was still WWF Champion.

This was the match that established Triple H as a permanent main eventer and was the beginning of the end of Foley’s full-time WWF career as he retired just two months later and would not return to the ring until March 2004.

A brilliant, bloody brawl, which is the template for all Street Fight matches that followed it.

#3 Shawn Michaels vs Triple H – SummerSlam (August 25, 2000)

Shawn Michaels vs Triple H SummerSlam 2002

Shawn Michaels had last wrestled for WWE at WrestleMania XIV when he dropped the WWF Title to Stone Cold Steve Austin in the headliner of the show.

Four years later, he returned to the ring to face his former D-X buddy, Triple H in a grudge match after ‘The Game’ had rammed Michaels’s head through a car window.

Fought under Street Fight rules, Michaels demonstrated that he had not lost a beat, in his first match of the 2000s, as he contested a hugely entertaining brawl against his former friend. The story of the bout was Michaels’s broken back and whether he could withstand the punishment Triple H inflicted on it. ‘The Cerebral Assassin’ revelled in battering Michaels’s Achilles heel at every opportunity, whilst ‘The Showstopper’ timed his sporadic comebacks to perfection. The highlight of which was a splash on Triple H through a table.

Michaels reversed a Pedigree into a pin for the upset win. Triple H in the post-match then smashed Michaels in the back with a sledgehammer to set up further matches between the pair later in the year.

As close to perfection as a wrestling brawl can be. Logical storytelling and first-class action make this a bonafide classic.

#2 Shawn Michaels vs Kurt Angle – WrestleMania 21 (April 3, 2005)

Shawn Michaels vs Kurt Angle 2000s

In 2005, Shawn Michaels and Kurt Angle had never collided in the ring. That was finally put right at WrestleMania 21 in an inter-brand match-up.

Their bout over 28 minutes was worth the wait. The story of the match was that Angle was viciously targeting Michaels’s bad back, whereas Michaels was living up to his moniker as “The Showstopper” and was pulling out huge moves when he made his comebacks.

The match began with both men attempting to outwrestle each other with fluid chain wrestling before the contest ramped up into higher-impact maneuvers. The closing stretch was epic as Michaels withstood the Ankle Lock and two Angle Slams, before he fell victim to another Ankle Lock.

The visual of ‘Mr. WrestleMania’ repeatedly trying in vain to escape the submission hold was immensely intense. Michaels finally accepted defeat and tapped out to give Angle the win after a truly epic encounter.

Crisp action and an emotional story that was paced to perfection. This was an incredible encounter and a highlight of the 2000s.

#1 Shawn Michaels vs The Undertaker – WrestleMania 25 (April 5, 2009)

Shawn Michaels vs The Undertaker

Shawn Michaels is a strong contender for wrestler of the 2000s, with a phenomenal record of endless superlative matches.

The peak was his first WrestleMania contest with The Undertaker, who himself had an excellent decade in the 2000s.

Michaels descended from the sky whereas ‘Taker rose from the depths highlighting the fact that both men were polar opposites. Heaven versus Hell as it were.

Packed full of huge moves, near falls, and excellent back-and-forth action, this was wrestling perfection. The match started slowly but upped the ante significantly down the stretch. The finish came when ‘The Phenom’ reversed a Moonsault attempt into a Tombstone Piledriver.

A staggeringly entertaining bout that has few equals. It was easily the finest match of the 2000s.

You can watch all of these matches exclusively on the WWE Network.