What if WWE lost the Monday Night War?

4. The Undertaker vs. Sting happens

The Undertaker vs. Sting is a dream match that never materialized, in part because WWE won

One of the biggest dream matches that wrestling has never seen, and is unlikely to see at this point was The Undertaker vs. Sting. The two guys were bona fide main event players for their respective companies and, particularly once WCW was meaningfully challenging WWE, they were each loyal company men who were among the few to never jump ship between promotions.

Sting had the opportunity to come to WWE after WCW closed its doors, but didn’t strike a deal for quite some time, and has cited in interviews that he wasn’t entirely sure he trusted WWE with the final years of his prime, and with his legacy. WWE had a brief window to get this match done between 2014 and 2016, but cast Sting against Triple H and later Seth Rollins instead. It’s still conceivable this match could happen, but Sting doesn’t seem too likely to wrestle again, and The Undertaker isn’t in a position to cover for his limitations.

Had WCW won the Monday Night War, there’s a very reasonable chance The Undertaker would have headed there for at least a short stint, as one of the biggest stars in wrestling, and with plenty of years left in his tank. Setting the match in WCW, we may not have gotten the best version of the match, but at least we likely would have seen it.