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#4 Sid
These days, having a WrestleMania main event usually means that you’re either a) the WWE Champion, or b) you’ve won the Royal Rumble.
Where Sid – be it Sid Justice, Sycho Sid or even Sid Vicious – is concerned, he’s main evented two WrestleManias in his career. The first of those came in 1992 with WrestleMania VIII as Sid battled Hulk Hogan, and then the Master and Ruler of the World would go on to defend the WWF Championship against The Undertaker at WrestleMania 13.
For his route to each and every WrestleMania that he competed at, however, Sid never managed to win a Royal Rumble contest. In fact, his greatest Royal Rumble match moment came during the beloved 1992 Rumble in which he eliminated Hulk Hogan literally seconds before he himself would be eliminated by Ric Flair as the Nature Flair notched up the W and the WWF Championship.
Given how great a shape the 58-year-old Sid is still in to this day, you can never bet against the former WWF and WCW World Champ turning up as a surprise entry in the Royal Rumble at some point – although even then you’d have to say there’s incredibly slim odds on the one-time Horseman managing to finally win a Royal Rumble contest.
