Nothing in wrestling is more satisfying to the fans than waiting for a series or trilogy of matches to pay off, with intriguing and engaging story lines that keep the fans invested. And there have been many examples throughout the entire wrestling world of both failed series where fans have not cared throughout, and successful ones where fans truly did not want them to end at all. From Ricky Steamboat and Ric Flair in the 80s to Samoa Joe and CM Punk in ROH, to AJ Styles and Christopher Daniels in TNA, the WWE is not the only place to witness such amazing series of matches, but it is the most prominent promotion with the biggest and most exciting superstars in the entire wrestling world.
In this modern world of WWE, where a greater focus of the product has been put on a more independent style of wrestling, as pure wrestling ability is now a greater asset to a superstar than it ever has been before, we are no doubt about to witness some great series of matches with the pushing of ‘the new era’ and new rivalries, with competitors such as Sami Zayn, Kevin Owens, Cesaro and AJ Styles being pushed more than ever before. The best example of this in recent memory is the upcoming third installment to the Finn Balor vs. Samoa Joe saga, which will be contested inside the first steel cage match in NXT history, and Sasha Banks vs. Bayley, who contested two of the greatest women’s matches of all time in 2015, helping establish the Women’s revolution in WWE.
Although some of these were contested over multiple years, and others over three straight Pay Per Views, these are the 12 best WWE match trilogies in recent memory, since the Attitude Era of the late 1990s and early 2000s.
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23 Batista vs. The Undertaker
One of the hardest and most sought after feats to achieve since the Attitude Ara is to earn the respect of industry icon The Undertaker, as many stars have been made in matches where the storyline is just that, earning his respect, most prominently Jeff Hardy and Brock Lesnar. Both this and the World Heavyweight Championship were at stake in 2007 when the men contested a WrestleMania match, as well as hard hitting TLC and Last Man Standing matches, which established Batista as a true star within the industry, as well as showcasing each and every skill of both very talented workers, which led to the 2007 Wrestling Observer Newsletter feud of the year.
21 The Undertaker vs. Brock Lesnar
Perhaps the most hyped trilogy on this list because of the monumental circumstances surrounding them (Lesnar breaking the streak which stood at 21-0), this series played out with ever improving matches each time these men got in the ring, culminating in the Undertaker’s specialty match, Hell in a Cell, which proved to be as brutal and devastating as it was awe-inspiring and emotion-educing for the audience. While both men’s age showed in their WrestleMania XXX encounter, the Undertaker returned in phenomenal shape for their Summerslam and HIAC rematches, putting on the hard hitting clashes that both men have become famous for throughout their respective WWE careers. While the decision to have already established Lesnar conquer the Undertaker will be questioned forever, what can’t be questioned is the fact these two icons of the business put on 3 hard hitting encounters, which brought major star power and validity to any card they appeared on, whether it be in 2002-3 or 2014-15.
19 CM Punk vs. Jeff Hardy
Perhaps no feud in recent memory has evoked more visceral emotions than this one, where CM Punk, playing the best heel in the business often critiqued Jeff Hardy for his reliance on drugs and belittled the crowd along with it, where Jeff played the perfect baby face hero as he has done his entire career. Despite the lines between kayfabe and real life being blurred throughout, especially with a YouTube video released by Hardy after his WWE release, this feud was as emotional as it was amazing in the ring, earning Wrestling Observer Newsletters Feud of the Year 2009, which featured one of the best one on one TLC matches in WWE history. While this may not have the hype and status of others on this list, the in-ring and promo quality of the entire feud has rarely been matched by anyone in WWE since.
17 Batista vs. Triple H
After turning on Triple H and the remaining members of evolution in 2005, declaring his intentions to stay on Monday Night Raw, breakout star Batista and veteran champion Triple H proceeded to have a fantastic rivalry over the World Heavyweight Championship with PPV matches at WrestleMania, Backlash and one of the most brutal Hell in a Cell matches ever seen in the third and final match at Vengance. The pair have become two of the biggest stars in the WWE since the attitude era, both transcending the in-ring wrestling world, as Triple H has moved on to becoming one of the best bookers in the game, and Batista has starred in several high profile movies. So it's safe to say the two will not be competing against one another any time soon, but the original trilogy which featured them both in their prime was one of the most hard hitting rivalries in all of wrestling.
15 Seth Rollins vs. Dean Ambrose
The rivalry which could define a generation (‘the new era,’ as WWE likes to push on the fans), Rollins and Ambrose have been clashing ever since the demise of the Shield in 2014, and fans were treated to many classic matches between the pair, including a ladder match for the WWE World Heavyweight Championship and a Hell in a Cell match, all of which Seth left the victor. Each match in their trilogy upped the anti and was one of the hottest rivalries in all of professional wrestling until Seth was injured late in 2015, and now with his return and hopefully impending face turn, this presents WWE with many options on how to continue the rivalry between these two former brothers, especially when their other brother Roman Reigns is added into the mix.
13 Sami Zayn vs. Cesaro
While these two had 4 televised matches between 2013-14 on NXT, it was Sami’s shock victory over Cesaro and two more matches, a televised 2 out of 3 falls match and a show stealer at NXT Takeover: Arrival that put this rivalry on the map as a defining one for the NXT brand, which put both Sami and Cesaro on the map as supreme in ring competitors. The two had fans hanging on their every move, every reversal and false finish, leaving fans hungry for more. And though the two have had limited interactions since Sami’s main roster arrival, WWE fans are no doubt waiting until the two can finally step in the ring together again, one on one.
11 Chris Jericho vs. Shawn Michaels
In 2008, Chris Jericho found a career renaissance through his heel turn on much loved HBK when he ‘accidently’ punched Shawn’s wife in the mouth, leading to some of the most personal, gripping television WWE has put on since the Attitude Era, culminating in an amazing ladder match for the World Heavyweight Championship. The hard hitting matches, the emotional promos and the heart wrenching twists and turns led to this being named the Feud of the Year in 2008 by the Wrestling Observer Newsletter, and was a chance for these two veterans of the industry to showcase the talents which have made them both legendary names in the wrestling business.
9 Kevin Owens vs. John Cena
While another example of ‘SuperCena’ rearing its ugly head, where he (or Vince McMahon) refuses to put over hot, new talent at the expense of the franchise player, this was still an amazing trilogy of matches to announce KO’s arrival on the main roster, where he secured a clean win over Cena in his first main roster match, which is almost unheard of in modern times. Together the two proved that you don’t need to put on an aerial classic or a hardcore massacre to be a great rivalry. As long as the fans are invested in the characters competing than it will be worth watching, but the in ring work of the matches none the less was stellar, as the chemistry between the two was fantastic, and will no doubt see the two tangle again in the future.
7 Hardy Boyz vs. Dudleyz vs. Edge & Christian
Arguably no teams in the history of WWE were more influential to the modern style of wrestling than that of the 3-way tag team rivalry that defined the attitude era, consisting of a 3-way ladder match at WrestleMania, followed by the first two Tables, Ladders and Chairs matches contested at Summerslam and the following WrestleMania. The fans never grew tired of seeing these teams battle it out, as the bar was raised each and every time weapons got involved with the teams, giving the audience moments that will last forever in WWE history, such as Jeff Hardy’s multiple swanton bombs from ladders, Jeff being speared by Edge while hanging onto the title 20ft in the air and all the career threatening falls each and every member of the rivalry took, solely for the respect of their peers, fans and championship gold.
5 John Cena vs. CM Punk
When CM Punk dropped his ‘pipe bomb’ in 2011, he began a white hot run which started with one of WWE’s only 5 star matches against John Cena at Money in the Bank, in a rivalry which blurred the lines of kayfabe and reality, making Punk an instant superstar and giving him a rivalry for life with whom he clicked like no other in his 8 year WWE tenure. The two would have another outstanding match at Night of Champions 2012, and then again on WWE Raw in 2013 in one of the best televised matches in recent RAW history, proving again why both men are regarded as two of the biggest stars in the industry during the PG era, as both are in a league of their own on the microphone and in the ring.
3 Steve Austin vs. The Rock
The two biggest stars in the industry's most fruitful era, perhaps of all time, faced off on countless occasions, but on the stage where it matters most, WrestleMania, the two men contested 3 battles, with Austin winning the first two and Rock finally overcoming his WrestleMania kryptonite and defeating Austin in their third and final Mania bout. While the matches were never likely to be top of any match of the year list due to the supreme cruiserweight and mid-card workers of the time, the two had the crowd eating out of the palm of their hands the entirety of the way, showcasing storytelling at its finest, as two of the greatest stars ever. The fans were truly invested the entire way, as evidenced by the popularity of the stars even today, almost a decade since their final WrestleMania encounter.
1 Shawn Michaels vs. The Undertaker
Way back in 1997 at Bad Blood, these two contested the first ever Hell in a Cell match, which was most memorable for the debut of Kane, and over a decade later, the two met in back-to-back WrestleMania matches, which arguably are the two greatest in the event’s history, showcasing what legends both these men are, as they were able to defy Father Time and put on classics like no one else in the history of the grand daddy of them all. While no where near the peaks of their careers, the two put on perfectly paced classics, featuring unmatched ring psychology and fluent, crisp exchanges which had the fans emotionally invested in both, not to mention the possibility of the streak and HBK’s legendary career both ending. Despite the Undertaker coming out victorious, this trilogy stands out as the greatest in WWE history for every reason, contested by two of the greatest wrestlers to ever walk planet Earth.
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