Wrestling Bios Presents - The History of Undertaker vs Shawn Michaels When the Heartbreak Kid Shawn Michaels faced The Undertaker inside a wrestling ring, magic would always happen. Undertaker vs Shawn Michaels was always abig draw, and the two men didn't dissapoint. From the first Hell in a Cell match in WWE history, a Casket Match that left Shawn Michaels with an injury so bad he would need to retire, to an outstanding Royal Rumble match finale, all the way to their WrestleMania classics at Wrestlemania 25 and 26. HBK vs Taker was always good. In this mini documentary, we look at all of the singles matches Shawn Michaels and Undertaker were involved in during their time in WWF / WWE. We look at In Your House matches, Royal Rumble Matches, Casket Matches, and retirement matches. #wwe #documentary #wrestling