* 27 years ago in 1988, the WWF ran the first ever SummerSlam live on pay-per-view from Madison Square Garden, making it the third PPV on the WWF's calendar. While it featured a few memorable moments on top, the card was oddly booked, feeling like a house show most of the way through.
In the main event, the Mega Powers (Hulk Hogan and WWF Champion Randy Savage) defeated the Mega Bucks (Ted DiBiase and Andre the Giant) with Jesse Ventura as guest referee. The build was all about two things: DiBiase bribing Ventura and the Mega Powers having some sort of secret plan involving Elizabeth in a bikini. So the big climactic moment was Liz taking her skirt off, distracting the heels. Hogan and Savage pounced, made their comeback, and when Ventura hesitated on the count, Savage slammed his hand down for the win. It was ridiculous, but it's one of the most famous finishes of the Hogan era, thanks in large part to being parodied on the cover of MAD Magazine.
The other big match saw The Ultimate Warrior squashing The Honky Tonk Man to win the WWF Intercontinental Championship in seconds. Brutus Beefcake had been "injured" by Ron Bass, so HTM issued an open challenge. After 15 months of terror (still the longest IC title reign), the fans at the Garden went completely nuts for Warrior and the title change. Warrior was cemented as a player and a big star, while HTM never really recovered, being moved way down the card.
* 23 years ago in 1992, the WWF ran SummerSlam at Wembley Stadium in London, England. The show aired live on Sky Sports in the United Kingdom, but the American pay-per-view broadcast was tape delayed two days, with the show airing in SummerSlam's then-traditional Monday night time slot. There were also three preliminary matches cut from the American broadcast. While the WWF claims that WrestleMania iII at the Pontiac Silverdome holds the company attendance record, it's been reported many times by Dave Meltzer of the Wrestling Observer that this show edged it by a few hundred fans, with the real number per internal WWE documentation being between 78,000 and 79,000 for both. The show was a legitimately huge event in the UK and represents the WWF's mainstream popularity peak in that part of the world.
The main event (though advertised as the semi-main event in the U.S.) and show closer saw "British Bulldog" Davey Boy Smith defeating Bret Hart to win the WWF Intercontinental Championship in a classic match. The storyline was that the Hart family, especially Diana (Bret's sister/Davey's wife) was being torn apart by the the title match, but of course all was well at the end. While there are other matches that are arguably better, in many ways this is the definitive Bret Hart match, representing his view of wrestling better than any other.
In the other key match, The Ultimate Warrior defeated WWF Champion Randy Savage by countout. It was pretty unprecedented for the WWF to do something like headlining with a pair of babyface matches, but this match had a unique hook: Ric Flair and Mr. Perfect were trying to convince each babyface that the other was turning heel and siding with them. Of course, neither did, and it led to Savage and Warrior teaming as the Ultimate Maniacs (sound familiar)? before Warrior was fired. While very different from the Savage-Warrior match at WrestleMania, it was another excellent bout and one of Warrior's very best.
* 21 years ago in 1994, the WWF opened up the brand new United Center in Chicago, Illinois with the seventh annual SummerSlam pay-per-view event.
All of the ads were built around The Undertaker vs. The Undertaker. See, months after The Undertaker...died...or whatever he did at the Royal Rumble, Ted DiBiase announced he was bringing the Dead man back. If he brought 'Taker to the WWF, why couldn't he bring him back? So he brought in Brian Lee as a fake Undertaker, Paul Bearer would dispute his authenticity, but it wasn't until the last big angle before the show that the crowd finally heard Mark Calaway's voice as The Undertaker promising to be at SummerSlam at Bearer's side. As for the match itself...planned special effects were nixed, so the 1994 version of 'Taker wrestled a lesser version of himself and it was exactly as awkward as it sounds. Lee lost and was never seen as the Underfaker again.
The other top match was Bret Hart defeating his brother Owen in a steel cage match. This one is very divisive: You either love or hate it. Bret felt that, in a WWF style cage match with no near falls and no blood, he and Owen had to tease as many near-escapes as possible, and they got 32 minutes to do so. It's unquestionably a about as good as a bloodless escape-only WWF cage match could get in 1994, but a lot of people aren't fans of that style. Regardless, the post-match angle was fantastic, with Owen and Jim Neidhart locked themselves in the cage with Bret as the rest of the Hart family tried to climb in.