The 2000s decade was a transformative one for WWE hoping to make changes and continue growing the brand. WWE scored a big victory by purchasing WCW and ECW to end the competition that existed in the 1990s. The brand split featured a new chapter of WWE trying to create their own competition.

Vince McMahon took more risks since there was no worry about another promotion giving them a real scare like WCW did. Quite a few matches showed the negative of that with less pressure put on the promotion to deliver strong results. The following bouts represented the worst things about WWE throughout the 2000s decade.

Vince McMahon Vs Stephanie McMahon

No Mercy 2003

The McMahon family becoming part of WWE TV in the late 1990s worked for the soap opera style of the Attitude Era. However, the constant stories involving Vince McMahon and his family started to jump the shark in the early 2000s when they kept coming up.

Stephanie McMahon’s underrated face tenure as Smackdown General Manager ended with her feuding against her father for refusing to follow his orders. A terrible “I Quit” match saw Vince destroying Stephanie by choking her out with a steel pipe.

Great Khali Vs Kane

WrestleMania 23

The lack of urgency with only TNA existing as a very distant competitor allowed WWE to run horrible programs without real concern over losing fan interest. WrestleMania 23 saw this with Kane and The Great Khali having one of the worst singles matches in WM history.

Vince McMahon’s love of giant wrestlers saw him forcing a feud between two struggling big men. Kane and Khali failed to get the crowd excited with their slow and boring match. Five minutes felt like twenty minutes for the slow match won by Khali.

Finlay & Hornswoggle Vs The Boogeyman & Little Boogeyman

No Way Out 2007

Bad comedy became part of WWE television with the use of little people in comedic angles. Hornswoggle made sense at Finlay’s sidekick, but WWE gave The Boogeyman a little person sidekick named Little Boogeyman solely to feud with each other.

No Way Out 2007 showed a terrible tag match with WWE expecting the fans to care about the bad comedy. Fans enjoyed Hornswoggle, but this was a bit too silly to have any realistic path towards getting over in a meaningful manner.

Edge Vs Triple H Vs Vladimir Kozlov

Survivor Series 2008

WWE started to pull more bait and switch storylines off in the 2000s when they had full power to take risks. Jeff Hardy was advertised to be in a triple threat WWE Championship match against Triple H and Vladimir Kozlov at Survivor Series 2008.

The story saw Hardy getting attacked and missing the match to have Triple H and Kozlov deliver a slow boring match for most of the time. Edge appeared at the end to enter the match replacing Hardy and winning the gold. Jeff appeared right after the match ended to make the logic even more questionable.

Teddy Long Vs Eric Bischoff

Survivor Series 2005

Authority figures started to become popular in the late 1990s, but WWE kept the storytelling role active for the entire decade of the 2000s. Raw and Smackdown becoming separate brands led to each show having an official General Manager.

Eric Bischoff and Teddy Long held the longest tenured roles for each show. WWE placed them in a non-wrestler vs non-wrestler match at Survivor Series 2005. The boring match featured the minimum entertainment value and made the show feel less important than in most years.

Goldberg Vs Brock Lesnar

WrestleMania 20

WWE went into WrestleMania 20 wanting fans to feel like it was the most important show in company history due to hitting the twenty-year mark. Brock Lesnar vs Goldberg was scheduled to being one of the most important matches of the night until both men revealed they were leaving the company after that match.

There was no way to fix the issue once fans discovered this and heckled them both. WWE having no competition saw them alienating some talents by flexing their leverage. Goldberg’s terrible 2000s WWE tenure ended with him winning an all-time bad match while fans booed him out of the building.

Mr. America Vs Roddy Piper

Judgment Day 2003

Veterans getting return stints in WWE became part of the 2000s since there was no longer any strong competition. Hulk Hogan and Roddy Piper both returned and crossed paths to play into their long-lasting history as iconic rivals.

Judgment Day 2003 featured their last high-profile match with Hogan under the Mr. America mask defeating Piper. Both men were already aging in WCW to have some terrible in-ring performances, and this featured them even older struggling to get by in a short match.

Miss WrestleMania Battle Royal

WrestleMania 25

The women’s division rarely got chances to succeed on the WrestleMania cards with battle royals and multi-person tag matches usually giving them minimal representation. WrestleMania 25 featured the lowest idea with the Miss WrestleMania Battle Royal involving the entire division.

Non-wrestlers like Tammy Sytch and Joy Giovanni made under the radar surprise appearances in the battle royal to show how WWE felt anyone could participate. Santino pretending to be a woman as Santina Marella won the battle royal to make it even more disrespectful to the women’s division.

The Undertaker Vs The Dudley Boyz

Great American Bash 2004

Goofy ideas like a concrete crypt match showed how poorly WWE was being run with awful creative concepts. The Undertaker faced the Dudley Boyz in a handicap match that featured Undertaker’s manager Paul Bearer stuck in a crypt and the threat of it being filled with concrete if he lost.

WWE delivered a terrible match as one of the worst PPV main events of the entire decade. The match lost all purpose afterwards when Undertaker filled the crypt to kill off Bearer’s character. Undertaker didn’t even turn heel since he wanted to shed his one weakness in a strange cruel payoff.

Triple H Vs Booker T

WrestleMania 19

The reign of terror is often considered the worst thing about WWE storytelling from the early 2000s. One program stands out more than others when looking back at why Triple H’s constant World Championship reigns became difficult for fans to watch.

Booker T becoming the #1 contender to challenge Triple H at WrestleMania 19 should have been a strong program. Instead, WWE turned it into Triple H making racially based comments to insult Booker. The boring match featured Triple H in control for most before winning cleanly to ruin any appeal of Booker getting revenge.