(4)Big Boss vs (13)Ridley 2018

Ulti's Analysis
Because of how Smash hype was clearly affecting this contest, paired with how Konami basically murdered Metal Gear Solid, there was a ton of fear that Ridley would be able to pull the upset. Turns out Ridley wasn't too big for Smash after all!

https://www.youtube.com/watch?v=IppO8vJP9WE

HE KILLED SAMUS! OH MY GOD HE KILLED SAMUS!!

But he couldn't kill Big Boss, or even get the board vote against him. This one was never close, though Ridley was clearly a step above from where he used to be, and Big Boss was clearly a step down. The effects of Smash and MGS's fates are pretty obvious, but they weren't going to close such a wide gap. For Big Boss, this match was a small measure of revenge for what happened in the Rivalry Rumble: https://gamefaqs.gamespot.com/poll/4561-southeast-division-final-samus-vs-ridley-big-boss-vs-the

Then again, does anyone care enough about the Rivalry Rumble to try getting revenge for it? Without looking it up, all I remember about that contest was Link winning, the Pokemon Trainers beating FF7 in a fake match, and Adolf Hitler making it into a GameFAQs contest match.

There weren't many bright spots for non-Smash characters versus Smash characters in this contest, and even some of the wins in that position were rough. But this was one of the few bright spots. We are in a time line where Ridley winning this wouldn't have surprised people, but Big Boss shot that one down immediately. Turns out the old dog can still hunt!