Goldberg vs. Undertaker & 7 Other Dream Matches We Got Way Too Late

The attraction bout between Goldberg and The Undertaker in Saudi Arabia showed just how badly things can go when a dream match comes too late. Fans have had strong desire to see certain matches between major names throughout the years. A dream match can be hit or miss depending on the timing of it coming to fruition.

The hope is that all matches deliver like The Rock vs Hulk Hogan at WrestleMania 18, but that best-case scenario is quite rare. Dream matches to come too late can lead to the talents being embarrassed for a poor performance. The following wrestlers were placed in terrible positions of having their dream matches coming too late.

8. Goldberg Vs The Undertaker

One of the biggest cautionary tales for wrestlers having a dream match late in their careers featured the Goldberg vs Undertaker debacle. WWE loves to book attraction matches between legends for the Saudi Arabia shows due to the money they make and the interest from the customers.

Goldberg and Undertaker taking the cash grab booking led to arguably the most embarrassing moment of their respective careers. Both men were struggling to get by and botched a few times. Goldberg almost injured Undertaker badly in the all-time bad match.

7. Sting Vs Bret Hart

WCW was criticized for booking too many veterans without trying to elevate new stars. 1998 was the year when they had a true dream match ready to go when Bret Hart was facing Sting for the first time at the Halloween Havoc event.

Both men used the same finisher of the Sharpshooter/Scorpion Death Lock and were among the most successful names of their generation. Unfortunately, the match was a bit too slow, prodding and featured the overbooking of the New World Order civil war at the time.

6. Kurt Angle Vs Chad Gable

An unlikely dream match scenario came towards the end of Kurt Angle’s WWE career when getting to work with some names of his choice. Chad Gable drew comparisons to Angle due to his wrestling background and fans wanted to see them mix it up.

Unfortunately, Angle had already lost a few steps and was struggling to have noteworthy matches. The bout was just fine as Angle scored the victory over Gable on free television. WWE planning out Angle’s final match with Baron Corbin took away from the final matches leading up to the end.

5. Shawn Michaels Vs Hulk Hogan

The egos of Hulk Hogan and Shawn Michaels were among the largest in wrestling to make a match between them even more enticing. WWE finally booked at SummerSlam 2005 almost a decade after it would have had a best-case scenario.

Hogan and Michaels showed the egos were still part of their identities when running into backstage issues. Michaels comically over-sold for Hogan during the match and took the loss showing displeasure. The anger of Michaels came from Hogan backing out of a rematch where he’d have put Michaels over to return the favor.

4. The Undertaker Vs Roman Reigns

WWE tried to make the most of The Undertaker’s legendary history at WrestleMania 33 when facing Roman Reigns in the main event. Undertaker’s streak ended two years prior to Brock Lesnar, but the match against Reigns was meant to give some finality to the legend’s career.

Roman and Undertaker had an all-time bad WrestleMania main event that made us all regret WWE booking it. Undertaker even expressed deep embarrassment and shame over his performance when discussing the night on The Last Ride documentary series.

3. Eric Bischoff Vs Vince McMahon

The idea of Vince McMahon and Eric Bischoff going at each other in a ring would have been must-see television in the late ‘90s. However, it didn’t have the same appeal when WWE actually booked the match in 2004, during Bischoff’s time as Raw General Manager.

The two former enemies had their match on Raw with Steve Austin as the guest referee. Unfortunately, it wasn’t as appealing and had a no contest finish with minimal impact. Brock Lesnar attacking Austin as the referee was the more noteworthy tale from the forgotten dream match.

2. Triple H Vs Brock Lesnar

The return of Brock Lesnar to WWE in 2012 has seen him around for a decade now achieving more than his first two-year run. One of the biggest dream matches on the table for Brock was a chance to wrestle with Triple H for the first time in a singles bout.

WWE booked the first match for SummerSlam 2012 for Lesnar to score the win in a lackluster outing. The trilogy of matches all disappointed with Paul Heyman and Stephanie McMahon’s involvement in promos being the peak. Brock and Triple H just didn’t have the chemistry to deliver what the audience wanted from them.

1. Bret Hart Vs Hulk Hogan

WWE reportedly wanted to have the huge match of Bret Hart being Hulk Hogan for the WWE Championship in the summer of 1993, but Hogan refused. Hart still went on to become the face of the company after Hogan left to eventually join WCW.

The end of Bret’s WWE run landed him in WCW as well as the next major name to jump ship. WCW booked the massive dream match on a random Nitro episode in 1998. The cheap finish of the New World Order interfering for yet another WCW main event DQ finish led to few fans even remembering Hogan vs Hart took place.