5 most bizarre WWE match stipulations in SummerSlam history

#2. Love Her or Leave Her Match at SummerSlam 1999

Stephanie McMahon on Monday Night RAW

Leading into the SummerSlam pay-per-view in 1999, Stephanie McMahon was dating Test. Stephanie's brother Shane felt that Stephanie was dating beneath the McMahon family standards. This resulted in a feud between Shane and Test.

Shane was aligned with the Mean Street Posse at the time, but eventually Stephanie had enough and told them to stay out of her business. Shane decided that the only way to settle it was for the first-ever 'Love Her or Leave Her' match at SummerSlam. If Shane won, Stephanie and Test could no longer see each other. If Test won, Shane would give them his blessing.

Shockingly, Test vs Shane McMahon was the best match on the SummerSlam 1999 card. They stole the show! pic.twitter.com/WJQt0XYy72

— Justin (@AllEliteJKT) March 27, 2021

The match eventually became a Greenwich Street Fight to add to the drama. Test picked up the victory went on to to continue his relationship with Stephanie McMahon. Of course, we all know what came next. Test and Stephanie were due to get married when Triple H appeared on the Titantron to announce that he had married Stephanie at a drive-thru wedding chapel in Las Vegas!

#OnThisDay in 1999.Stephanie McMahon was set to marry Test on Monday Night #Raw.But Paul "Triple H" Levesque had a very important announcement to make... pic.twitter.com/BSvkQAIAfb

— Just Talk Wrestling (@JustTalkWrestle) November 29, 2017

Oh how we miss the Attitude Era and these bizarre stipulations!