#4 Shane McMahon gave The Undertaker a gift (WWE WrestleMania 32)
Shane McMahon competed in his first WWE match in almost seven years when he fought The Undertaker at WrestleMania 32. The 30-minute Hell in a Cell match, which The Undertaker won, is best remembered for McMahon jumping off the top of the steel structure.
In 2020, the man behind The Undertaker persona, Mark Calaway, began discussing his WWE career in out-of-character media interviews. He also opened up about his difficult retirement decision in the Last Ride docuseries on the WWE Network.
Ahead of one of the Last Ride episodes, McMahon wrote an article for ESPN about his friendship with The Undertaker. He revealed in the article that the two men exchanged gifts after their WrestleMania 32 match.
“I always have extra baseball jerseys made for important events, so I presented one to him after the match, and as I was doing that, he was giving me one of his [MMA-style] gloves. That old-school appreciation.”
Three years later, the long-time friends shared the ring again at WWE Extreme Rules 2019. On that occasion, The Undertaker teamed with Roman Reigns to defeat McMahon and Drew McIntyre in a tag team match.