From body slams to broken hearts, SummerSlam has always been WWE’s midsummer proving ground. Since 1988, this annual event has delivered unforgettable moments, classic matches, and storyline shifts that have redefined careers. At Back Sports Page, we’re diving deep into every SummerSlam in history—breaking down the main events, spotlighting the must-watch bouts, skipping the filler, and analyzing the aftermath that shaped the future. Whether it’s legends colliding, titles changing hands, or unexpected swerves, this series captures it all. Welcome to the ultimate retrospective on The Biggest Party of the Summer.
Venue: Target Center, Minneapolis, Minnesota
Date: August 22, 1999
Attendance: 17,370
MAIN EVENT:
Stone Cold Steve Austin (WWF Champion) vs. Triple H vs. Mankind (WWF Championship – Triple Threat Match)
Special Guest Referee: Jesse “The Body” Ventura
With Governor Jesse Ventura stepping in as the guest referee, the main event of SummerSlam ‘99 had major mainstream buzz. Originally promoted as Austin vs. Triple H, the match became a triple threat after Mick Foley was added late in the build.
The match was chaotic, filled with Attitude Era brawling, signature spots, and big personalities. In a swerve finish, Mankind pinned Austin (not Triple H), winning the WWF Title—though the reign lasted barely 24 hours. The next night, Triple H attacked Mankind and won the title on Raw, kicking off his reign of terror and transition into a true main event player.
Why it Mattered:
This match was the torch-passing moment for Triple H. While he didn’t win at SummerSlam, the angle launched his dominance for the next year. It was also Austin’s final SummerSlam as a full-time performer, as neck issues continued to slow him down. Ventura’s involvement gave the WWF a shot of mainstream political crossover appeal.
WHAT TO WATCH:
1. Test vs. Shane McMahon (Love Her or Leave Her Greenwich Street Fight)
This might be the most underrated match of the Attitude Era. A wild, emotionally charged brawl with stiff shots, dramatic storytelling, and an invested crowd. Test’s win—fighting for Stephanie McMahon—was career-defining, and Shane took huge bumps throughout.
2. Jeff Jarrett vs. D’Lo Brown (Intercontinental & European Titles – Winner Takes All)
A strong opener with solid pacing and heel antics. Jarrett regained the IC title with help from Debra, setting up his misogynistic gimmick that would soon define his WWF exit. D’Lo was always a workhorse, and this match proved it.
3. Chris Jericho’s SummerSlam Debut (Backstage Promo)
While not a match, Jericho’s brief backstage segment with Howard Finkel showcased the early seeds of his WWF persona. It reminded fans that big things were coming from Y2J.
WHAT TO SKIP:
Al Snow vs. Big Boss Man (Hardcore Title)
While this feud would escalate in disturbing ways (hello, Pepper), this match was mostly gimmicks and bad camera work. The “Hardcore Title in a bar” vibe was fun in theory, but poorly executed here.
The Undertaker & Big Show vs. X-Pac & Kane
An awkward tag match with clunky pacing. It’s worth watching for storyline developments involving Kane, but as a match, it lacked chemistry and clarity.
AFTERMATH:
SummerSlam 1999 helped usher in the next wave of main eventers. Triple H’s ascension began in earnest, Test earned fan respect, and the McMahon family drama continued to take center stage. Austin’s presence still loomed large, but change was in the air.
This event also marked the final SummerSlam of the 1990s—closing a chaotic, groundbreaking decade where WWF transitioned from cartoonish to cutting-edge, from family-friendly to attitude-heavy. And by this point, there was no looking back.
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