At Wrestlemania 32 this weekend, Shane McMahon will return to the ring for a match against the event's most iconic figure—the Undertaker. It won't just be any match, but a one-on-one encounter inside Hell in a Cell, a 20-foot high steel structure the Undertaker made famous when he hurled Mick Foley from the top of it in 1998. At stake for McMahon in this bout? An opportunity to control the WWE's flagship program, Monday Night Raw. For the Undertaker, a loss means that his storied career will finally come to an end.

When Shane walks the aisle on Sunday, we'll have the answer to the most important question in all of this—which sneakers will he wrestle in? Since making his in-ring debut in 1999, Shane-O-Mac has been a surprisingly dedicated sneakerhead, competing in some of the greatest pairs Nike and Jordan Brand have to offer. He didn't miss a beat when he recently returned to Raw after a six-year absence, doing so in the always-appropriate Air Jordan 1. That move, presumably, landed him a spot on Jordan Brand's seeding list.

Before we find out what Shane has lined up for 'Mania, here's a look at his greatest sneaker moments inside the squared circle.