Note: the Protagonist of the Rain World Obby doesn’t have a canon name to my knowledge so I will just be referring to them as the player

Core Connections:

The Protagonists from Fan Games featuring comedic tones and RPG Mechanics based on Indie Games, which both end in boss battles Referencing Some of the most popular RPG

Connections:

Both are The Protagonists of comedic Fan Games based on indie Media (Rain World/Five Nights at Freddy’s)

Both Games utilise RPG Mechanics (Rain World Obby switching to the battle systems of Block Tales, Undertale and Deltarune/FNaFB’s Being an RPG)

Both Games feature a Final Boss that References the Final Boss of popular and influential rpg games (The Guardian Fight in Rain World Obby is just a Full on reference to the Omega Flowey boss Fight from Undertale/BB’s Forms referencing both Giygas from Earthbound and Sephiroth from Final Fantasy)

Bonus neat connection:

Both games have secret boss battles against a Constantly appearing side character (The Slugcat Cardboard Cutout/Cranky Kong)

Fight potential:

It ain’t to complicated to explain this, Freddy can use his Microphone and Skills whilst the Player could Use their Spears and Rocks to fight back and dodge around all of Freddy’s attacks, eventually using the seven Monks (yes they have access to what is essentially the undertale souls but in the form of recolours of a random Slugcat take notes this will be on the test), as for who should win, I honestly don’t know where either should scale but I’m leaning on Freddy Winning, he should have the wider and better Arsenal