Jake “The Snake” Roberts vs. Andre The Giant (WrestleMania 5)

When Andre The Giant took on Jake Roberts at WrestleMania 5, Andre’s health was on the decline, and this was on full display in the matchup. Roberts tried his best, but the match was a burden to sit through at nine-minutes. The match ended in a DQ victory for Roberts, when Andre decided to attack the guest referee, Big John Studd.

Bret Hart vs. Vince McMahon (WrestleMania 26)

Whilst nobody expected a wrestling classic going into Bret Hart vs. Vince McMahon at WrestleMania 26, it’s fair to say that nobody was expecting one of the most lifeless matches in WrestleMania history. The match was vastly overbooked with complex, nonsensical twists, and the crowd were silent as Hart just worked over McMahon for 10-minutes before making him submit to the Sharpshooter.

The Miz vs. Snoop Dogg (WrestleMania 39)

WrestleMania 39 saw the impromptu return of Shane McMahon to challenge The Miz. Seconds into McMahon’s return matchup, he tore his quad, and this forced WWE to have Snoop Dogg virtually take over in the match. Snoop Dogg would punch The Miz twice, before delivering an atrocious looking People’s Elbow to pin the former WWE Champion.

Brock Lesnar vs. Goldberg (WrestleMania 20)

Quite rightly, there was a ton of hype heading into Brock Lesnar vs. Goldberg at WrestleMania 20. Unfortunately, due to the Madison Square Garden fans being aware that both men were leaving the company, they decided to turn on both talents, and this made both men lose complete focus. The match featured endless stalling, and a crowd that were more interested in seeing the guest referee, Stone Cold Steve Austin. The finish came when Goldberg pinned Lesnar after a Jackhammer, and this officially marked the end of both men’s first respective runs in the company.

Brock Lesnar vs. Roman Reigns (WrestleMania 34)

WWE set themselves up for failure at WrestleMania 34. The main event of the show saw Brock Lesnar defend the Universal Title against Roman Reigns, and the match was abysmal. This came at a time when fans loathed Reigns’ babyface act, and the feud between Reigns and Lesnar lacked any type of spark.

The fans heckled the match with negative chants, and the quality of the match made Lesnar so angry that he threw his Universal Title at Vince McMahon backstage.

Kane vs. The Great Khali (WrestleMania 23)

WrestleMania 23 featured some excellent in-ring work from matches such as Batista vs. The Undertaker and John Cena vs. Shawn Michaels. Unfortunately, the acclaimed show also featured a truly horrific matchup between Kane and The Great Khali. The match only existed so Kane could body slam Khali, and outside of that, the quality of the action was not deserving of a WrestleMania spot.

Vince McMahon vs. Pat McAfee (WrestleMania 38)

In an impromptu match at WrestleMania 38, Vince McMahon challenged commentator, Pat McAfee. This match would act as McMahon’s final WWE match, and it was without a doubt his worst. Even though McAfee had just defeated a full-time star in Theory, he was unable to defeat McMahon, as McMahon kicked a football at him.

The Undertaker vs. Big Boss Man (WrestleMania 15)

When WWE announced a Hell in a Cell match for WrestleMania 15, fans were excited. Attitude Era Hell in a Cell matches made up for some of the most iconic matches of the respective era, and having two powerhouses in The Undertaker and Big Boss Man had great potential.

Unfortunately, the end product was one of the most boring cell matches possible. The match was met with silence from the crowd, as they were confused as to who was the heel and who was the babyface, and the match (outside of being bad), is mostly known for The Undertaker hanging Boss Man after the match.

The Undertaker vs. Giant Gonzalez (WrestleMania 9)

Although The Undertaker had numerous classics at WrestleMania, he also had his fair share of stinkers. At WrestleMania 9, WWE decided to pair the legendary wrestler with Giant Gonzalez. Gonzalez was below average in the ring, and he had a laughable gimmick that wasn’t over. As was typically the case with larger-than-life wrestlers such as Gonzalez, WWE were insistent on doing everything they could to get them over. This meant that instead of having The Deadman defeat the virtually immobile Gonzalez clean, he had to win via DQ to keep some of Gonzalez’ credibility intact.

The Bushwhackers vs. The Fabulous Rougeaus (WrestleMania 5)

WrestleMania 5 featured a match that was so horrendous, that Dave Meltzer from The Wrestling Observer awarded the match a minus-4 rating. The match was between The Bushwhackers and the Fabulous Rougeaus. The match featured poor comedy, a lack of selling, and a crowd watching on that simply didn’t care.

Miss WrestleMania Battle Royal (WrestleMania 25)

Upon the announcement of the Miss WrestleMania battle royal at WrestleMania 25, fans hoped that the match would act as a celebration of the women of WWE, both past and present. Sadly, WWE had other ideas. The women all came out as one collective unit, this meant that nobody could genuinely tell who was in the matchup. The match featured legends such as Torrie Wilson and Molly Holly, yet they barely received any acknowledgement. The match was won by Santino Marella in drag, which was a massive spit in the face towards the fans, and of course, the women in the matchup.  

Tori vs. Sable (WrestleMania 15)

Before the likes of Lita and Trish Stratus arrived in WWE, the women’s division was in a poor state filled with lacklustre matches, and characters that couldn't wrestle. At WrestleMania 15, Sable collided with Tori for the Women’s Title, and the match featured one woman who refused to take any bumps in Sable, and another woman in Tori who had zero idea what was going on. Even Michael Cole on commentary was trying to justify the lousy action by claiming that Tori was “inexperienced”, which was a complete understatement.  

Jerry “The King” Lawler vs. Michael Cole (WrestleMania 27).

The build towards Jerry Lawler and Michael Cole dominated airtime heading into WrestleMania 27, and it was almost as if the fans gave WWE a pass, as they expected the WrestleMania match to be a short and sweet affair with Lawler getting the win. Additionally, the added element of Stone Cold as guest referee was enough to warrant some level of interest. The match itself was a complete failure, as WWE devoted over 13-minutes to a match that was filled with horrendously executed comedy, and a crowd that didn’t care one bit about the action.

The match was universally hated by the fans, and even former WWE Chairman, Vince McMahon labelled the match as the worst match he’s ever seen, which was a fair assessment. The match ended when Cole won via DQ, and this was done so WWE could continue the feud for several more agonising months following WrestleMania.

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