#27 Hulk Hogan and Brutus Beefcake vs. Randy Savage and Zeus - Summerslam 1989

For everything the tag-team main event of Summerslam 1988 was, the match a year later was not. Despite having both Hogan and Savage in this, neither of the former Mega-Powers could hide the fact that Vince McMahon decided it would be a good idea to feature Zeus on such a grand stage.
The match was forgettable at best and did nothing for anyone involved. Even at the height of Hulkamania, the company could still make some terrible decisions.
In fact, the only thing you need to go back and watch when it came to this feud is the hilarious promo that Savage, Zeus and Sensational Sherry cut. Seriously, go check that out.
#26 The Elimination Chamber - Summerslam 2003

Almost everything about the Summerslam 2003 main event inside the Elimination Chamber was a huge disappointment. For all the Elimination Chamber at Survivor Series 2002 was, the repeat at Summerslam simply was not. The fact that the whole affair took less than 20 minutes is a joke in itself, but the real problem was who ended up winning.
The fans were clearly ready for Goldberg to take his rightful place as champion here, but unfortunately for him and everyone else in the arena, this was the Triple H burial era of the WWE and nothing was going to get past that.
This match was irrelevant but at least it had some decent action for the most part.
#25 The Undertaker vs. ''The Undertaker'' - Summerslam 1994

This bout from Summerslam 94 can be filed in the 'at least they tried' category. The Undertaker was clearly somebody the WWF saw as having a bright future, and it was right to try and place him in as many main events as possible around this time.
Unfortunately, we were starting to get into the New Generation era of the company and the writing ability just wasn't what it once was.
The fact that this match main evented a show that also had Owen and Bret Hart square off inside a steel cage didn't help matters. After the drama of that classic, nobody really wanted to watch The Undertaker attempt to carry a semi-talented jobber to a passable match.