25 Greatest WWE SummerSlam Matches EVER

20. Shane McMahon Vs Test (SummerSlam 1999)

CM Punk Brock Lesnar
WWE.com

The best match by miles on a wretched SummerSlam card at the height of Vince Russo's influence in WWE, Test and Shane McMahon's energetic brawl brought the best out in 'The Money' as well as the former headline prospect.

Utilising a host of weapons and high spots as well as the Mean Street Posse and The Stooges, this was a belt-and-braces belter that didn't shy away from shortcuts if they expedited the journey to such a satisfying destination. Shane doled out his first elbow to the commentary desk whilst Test pierced the heart of his real-life mate with his own from the top rope to proffer the gripping conclusion.

Babyface Stephanie McMahon even added much to the proceedings - the inspired "love her or leave her" stipulation attached to the clash resulted in her relationship with Test continuing as she'd hoped. Her wild run to the ring to celebrate sold the result almost as well as her brother's bruising demise.

Contributor
Contributor

Michael is a writer, editor, podcaster and presenter for WhatCulture Wrestling, and has been with the organisation nearly 8 years. He primarily produces written, audio and video content on WWE and AEW, but also provides knowledge and insights on all aspects of the wrestling industry thanks to a passion for it dating back over 35 years. As one third of "The Dadley Boyz" Michael has contributed to the huge rise in popularity of the WhatCulture Wrestling Podcast and its accompanying YouTube channel, earning it top spot in the UK's wrestling podcast charts with well over 62,000,000 total downloads. He has been featured as a wrestling analyst for the Tampa Bay Times, GRAPPL, GCP, Poisonrana and Sports Guys Talking Wrestling, and has covered milestone events in New York, Dallas, Las Vegas, Philadelphia, London and Cardiff. Michael's background in media stretches beyond wrestling coverage, with a degree in Journalism from the University Of Sunderland (2:1) and a series of published articles in sports, music and culture magazines The Crack, A Love Supreme and Pilot. When not offering his voice up for daily wrestling podcasts, he can be found losing it singing far too loud watching his favourite bands play live. Follow him on X/Twitter - @MichaelHamflett