Ranking 31 Years of WWE Summerslam Main Events (1988-2018)

#20-16

The Undertaker punishes his challenger, Bret Hart

#20 1997 - The Undertaker vs Bret 'Hitman' Hart

The best match of Undertaker's 1997 Championship reign was the one in which he dropped the belt to Bret Hart. The match was entertaining but at 28 minutes in length was at least five minutes too long.

However, the match is best remembered for the finish in which Bret Hart spat in the special referee, Shawn Michaels's face. Michaels attempted to hit Hart with a steel chair but Hart ducked and Michaels clocked Undertaker instead. Three seconds later, Hart was the new champion.

#19 2006 - Edge vs John Cena

Although Edge and John Cena were a terrific in-ring combination, this encounter with Edge's WWE Championship on the line is one of their least remembered clashes.

It also finished in a screwjob when Edge smacked Cena in the back of the head with brass knuckles for the win. Their TLC rematch a month later was far superior to this one.

#18 2004 - Chris Benoit vs Randy Orton

Randy Orton's first World Championship reign is seldom mentioned on WWE television due to the fact he won it from double-murderer, Chris Benoit. Orton, the heel, was predominantly cheered in the match as fans were keen to see him make history as the youngest World Champion ever in WWE.

The match was decent due to the high calibre of the participants but it was far from a classic.

#17 2007 - John Cena vs Randy Orton

Back in 2007, a clash between John Cena and Randy Orton was a much-anticipated one. Orton's one and only World title reign occurred exactly three years earlier in the match with Benoit. It had lasted a month.

Cena had been champion for almost a full year at this point and fans were anticipating a title change. It didn't happen. Cena won the match and defended the title. Orton would be made to wait another two months before tasting another World Championship. It was a good match but the two would have many better.

#16 1998 - Stone Cold Steve Austin vs The Undertaker

In the summer of 1998, the WWF was the hottest ticket in town and Stone Cold and Undertaker were it's biggest stars. Although, the two had clashed before, never had the hype been so great.

Unfortunately, the match while it had his moments, was a disappointment, namely due to Austin suffering a concussion early in the match which caused his timing to be off for the remainder of the clash. Stone Cold earned the win with the Stunner, defending his WWF Championship.