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The Last 10 Losses Of Shawn Michaels' WWE Career

Shawn Michaels is one of the greatest wrestlers of all time. The Heartbreak Kid is an exceptional in-ring performer, and he has been involved in many epics throughout his career. However, Michaels spent four years on the sidelines after WrestleMania 14 until SummerSlam 2002 as he sustained a serious back injury in a casket match with The Undertaker at the 1998 Royal Rumble. Nevertheless, Michaels picked up right where he left off when he returned and he didn't lose a step in the squared circle.

RELATED: 5 Shawn Michaels Matches Dave Meltzer Overrated (& 5 He Underrated)

Despite earning a lot of wins in his career, Michaels isn't exempt from coming up short in some matches. Michaels reunited DX with Triple H in 2009, and Michaels was involved in a lot of tag team competition. Nonetheless, HBK lost several matches on his way out, with some defeats more significant than others.

10 W/ Triple H Vs. Legacy - Breaking Point 2009

Legacy v DX Breaking Point 2009 Cropped

There were a unique Submissions Falls Count Anywhere match between DX and Legacy at Breaking Point 2009. The chemistry between both teams was remarkable, and both teams had a lot of offense in this bout which lasted a little over 20 minutes.

RELATED: 10 Matches You Forgot Shawn Michaels Competed In

DX prevailed in their previous meeting at SummerSlam, but Legacy flipped the script in Montreal. Cody Rhodes applied a Figure Four Leglock around the ring post whilst DiBiase cinched in the Million Dollar Dream leaving Michaels no choice but to tap out.

9 W/ Team Raw Vs. Team SmackDown - Bragging Rights 2009

Team Raw v Team SmackDown Bragging Rights 2009

Battle for brand supremacy at Bragging Rights between Team Raw and Team SmackDown. Raw fielded Shawn Michaels, Triple H, Big Show, Cody Rhodes, Jack Swagger, Mark Henry, and Kofi Kingston. Representing SmackDown was Chris Jericho, Kane, Finlay, R-Truth, Matt Hardy, and the Hart Dynasty.

This bout only lasted 15 minutes, and it was a decent match between the two teams. However, the World's Largest Athlete cost his team as he helped out Jericho, who was his tag team championship partner, and Team SmackDown was triumphant.

8 W/ Triple H Vs. John Cena & The Undertaker Vs. Jeri-Show - Raw (11/16/09)

DX v John Cena & The Undertaker v Jeri-Show Raw November 16, 2009 Cropped

There was firepower on show on the November 16, 2009 episode of Raw. Six former World Champions were featured with DX going head-to-head with the reigning WWE Champion John Cena and the World Heavyweight Champion The Undertaker, and the Unified WWE Tag Team Champions Jeri-Show in a triple threat tag team match.

RELATED: 10 Cringey DX Moments We Completely Forgot About

This match took place in Madison Square Garden. Michaels upped the tempo when he was involved in the match. Nevertheless, Jericho took Michaels out with the codebreaker. Cena put Triple H away with the AA to pick up the win for himself and the Phenom.

7 Vs. John Cena Vs. Triple H - Survivor Series 2009

Cena v Michaels v Triple H Survivor Series 2009 Cropped

One of the biggest main events in the history of Survivor Series featured John Cena defending the WWE Championship in a triple threat match against Shawn Michaels and Triple H. Survivor Series has been kind to Michaels as he won his final two World Championships at the event.

The Heartbreak Kid threw a spanner in the works as he connected with Sweet Chin Music on Triple H right from the word go. The match was fantastic with three of the all-time greats functioning at the top of their games. Ultimately, Cena battled past Michaels and Triple H to remain as WWE Champion.

6 W/ Triple H Vs. Jeri-Show - Raw (12/14/09)

DX v Jeri-Show Raw December 14, 2009 Cropped

Shawn Michaels and Triple H finally won the Unified WWE Tag Team Championship together when they beat Jeri-Show for the gold in a TLC match at TLC 2009. 24 hours later, Jeri-Show was looking to regain the titles against DX on Raw.

This match was a complete waste of time. Jeri-Show was the Slammy Award winner for the Tag Team of the Year. The match barely got going with Triple H pushing the referee who fell over Michaels. Jeri-Show prevailed, but DX retained their titles by disqualification.

5 Royal Rumble Match - Royal Rumble 2010

Shawn Michaels Royal Rumble 2010 Cropped

Shawn Michaels won the Royal Rumble match in back-to-back years in 1995 and 1996, and he was seeking a third triumph as he desperately wanted to face The Undertaker at WrestleMania 26. HBK entered his final Rumble match as the 18th participant.

HBK was a man on a mission, and he eliminated Ted DiBiase, Cody Rhodes, John Morrison, Carlito, and Drew McIntyre. It was every man for themselves, and HBK eliminated Triple H from proceedings. Nonetheless, Michaels had to find another avenue to face Undertaker as Batista eliminated him from the Rumble.

4 Vs. Randy Orton - Raw (2/1/10)

Shawn Michaels v Randy Orton Raw February 1, 2010 Cropped

The winner between Shawn Michaels and Randy Orton would advance to the Elimination Chamber match for the WWE Championship at the inaugural Elimination Chamber event. Moreover, Michaels was desperate to face the Phenom at WrestleMania 26.

Orton and Michaels were no strangers to each other, and the Viper got the upper hand early on.HBK had some offense but Orton prevailed with a roll-up out of nowhere leaving Michaels' plans for WrestleMania up in the air.

3 W/ Triple H Vs. ShoMiz Vs. The Straight Edge Society - Raw (2/8/10)

DX v ShoMiz v The Straight Edge Society Raw February 8, 2010 Cropped

DX defended the Unified WWE Tag Team Championship against ShoMiz and the Straight Edge Society's CM Punk and Luke Gallows in a triple threat elimination match. This bout was competitive with all three teams giving it their all. Punk attempted the GTS but Michaels connected with Sweet Chin Music to remove him from the equation.

Miz was going for the Skull Crushing Finale on Michaels but he fought out of it. However, Michaels hit Show with Sweet Chin Music. There was a mix-up between DX, and Miz rolled up Michaels to clinch the Unified WWE Tag Team Championship.

2 W/ Triple H Vs. ShoMiz - Raw (3/1/10)

DX v Jeri-Show Raw March 1, 2010

DX dropped the Unified WWE Tag Team Championship to ShoMiz, and they attempted to regain the titles on the March 1, 2010 edition of Raw. This was Michaels' final match on Raw before his retirement. Moreover, ShoMiz isolated Triple H in their corner.

The Game managed to tag in Michaels, and Michaels connected with Sweet Chin Music when the referee wasn't looking. Moreover, HBK was in cruise control but he was distracted by Undertaker who appeared on the titantron. Miz took advantage of the situation, and he retained the titles for his team with a rolling jackknife cover.

1 Vs. The Undertaker - WrestleMania 26

Undertaker v Shawn Michaels WrestleMania 26 Cropped

Shawn Michaels got his wish after he cost The Undertaker the World Heavyweight Championship at Elimination Chamber 2010. The legends squared off at WrestleMania 26, which was their second successive meeting on the Grandest Stage of Them All.

There was a caveat as Michaels' career was on the line as Undertaker's unbeaten streak. This match was off the charts, and it was another classic between the two. Michaels threw the kitchen sink at Undertaker, but it wasn't enough with the Deadman putting Michaels out of his misery with a jumping Tombstone.