Twilight Sparkle (mlp) vs Harry Potter  
(magically gifted students, have defeated high-level threats in the past)
 
John Egbert (homestuck) vs Aang (avatar)  
(main element is the wind)
 
Finn & Jake (adventure time) vs Link (legend of zelda)  
(young swordsmen from fantasy-adventure settings)
 
Sonic the Hedgehog vs Rainbow Dash (mlp)  
(blue, attitude, known for their speed, have defeated high-level threats in the past)
 
The Doctor vs Dave Strider (homestuck)  
(both d with time travel and utilize unusual-seeming objects to do so (The Doctor via the TARDIS, Dave via his Time-Tables))
 
Superman vs Luke Skywalker (starwars)  
(reference to YourFavoriteMartian’s Nerd Rage video: “and a Jedi could whip Superman in a fight, when i’m right imma laugh like (NERD laugh)”)
 
Marceline (adventure time) vs Kanaya Maryam (homestuck)  
(vampires, dual-purposed weapons (Marceline’s axe-bass, Kanaya’s lipstick/chainsaw))
 
Shadow the Hedgehog (sonic) vs Experiment 627 (lilo & stitch)  
(artificially created lifeforms that are the strongest of their kind)
 
Prince Zuko (avatar) vs The Pyro (tf2)  
(main element is fire, LOTS of fans)
 
Meloetta (pokemon) vs Hatsune Miku (vocaloid)  
(main element is music, kawaii-desu, reference to the Meloetta: Melody of Discord fangame)
 
Reimu (touhou) vs Dark Magician Girl (yugioh)  
(high-ranking magical girls in their own settings (Reimu as a Shrine Maiden, DMG as student of Priest Mahado in her past life))
 
Applejack (mlp) vs Hungary (hetalia)  
(independent to an extent (Applejack claiming to buck the entire orchard on her own in Applebuck Season but eventually caved and asked for her friends’ help, Hungary and Austria have long-since divorced but still treat eachother as a couple))
 
Vriska Serket (homestuck) vs America (hetalia)  
(egotistical, very few can stand them in-universe, but they have their fair share of fans IRL)
 
Flame Princess (adventure time) vs Katniss Everdeen (hunger games)  
(pun involving “girl on fire”)
 
Stitch vs Zim  
(main-title aliens debuting in the early 2000s)
 
King Sombra (mlp) vs The Lich (adventure time)  
(undead dark lords sealed away for at least a millennia (The Lich in amber beneath the candy castle, King Sombra in the northern ice))
 
 
-DLC Rivalries (AT SOURCE ONLY)-
 
Pinkie Pie (mlp) vs Kirby  
(pink, can eat seemingly endlessly, have defeated high-level threats in the past)
 
Draco Malfoy (harry potter) vs Eridan Ampora (homestuck)  
(wizardy rivals, opposing views on magic)
 
Lion-O (thundercats) vs He-Man (masters of the universe)  
(80s muscular swordsman icons)
 
Ganondorf (legend of zelda) vs Gunter (adventure time)  
(high-level evils (Ganondorf being the King of Evil, and Gunter being stated as the most vile creature in all of ooo))

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Background Pony #3ECE
Whoa, someone else ed the Lilo and Stitch show?! That was like crack cocaine for furries back in the day. And Stitch still monopolizes all of Japan…
@smashfan666  
Well, you know, he doesn’t have to be the exact size. After all, in Smash Bros, Olimar and his Pikmin were scaled up from their actual sizes (which is actually smaller than a Gamecube Memory Card!), plus this wouldn’t be the first time some Transformers characters were scaled down to fight opponents that would normally be MUCH smaller than them. Look up DreamMix TV World Fighters, a Japan-only game that played basically like Smash Bros!
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
SECRET CHARACTER! rivaly: Ladybug (Miraculous Ladybug) vs. Star Butterfly (Star vs. the Forces of Evil)
 
…Sorry, got caught up in it…
 
@smashfan666  
That’s a perfectly reasonable explanation, though you could probably get away with scaling them down to something more reasonable. Or using characters from the Beast Era, when everyone’s smaller. If you wanted to use them, I mean.
smashfan666
The End wasn't The End - Found a new home after the great exodus of 2012

Fandom Drifter
@mdalsted  
no, it’s just that playing as any transformers character that isn’t a human would pose an incredibly unfair scale-based advantage.
 
…i mean, there COULD have been a playable mini-con or heaster, but i know people, and people don’t want to play as THAT, they want to play as the frickin’ semi. or at least the tape player.
I picture this as a tournament. The grid is laid out with eight match-ups on each side, said match-ups being the rivalries mentioned in the description. Who will reach the center of the grid?
@Scrounge  
Guess the person who made this picture isn’t a big fan of Transformers. (shrug) That’s my guess, anyway.
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
@Background Pony #6A78  
That means nothing to me.
Background Pony #A494
@Scrounge  
Transformers = Ridley
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
@Background Pony #76F2  
Why no Transformers at all?
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
This will end in tiers.
Background Pony #DB7B
Why only one Touhou?
@Plasma Blade  
And Samurai Jack.
Throw in Sakura kinomoto, El Santo, and Lloyd Irving from Tales of symphonia and I’m In.
Background Pony #9AAF
I CANT CHOOSE. OMG JOHN AND DAVE. WHY I HAVE TO CHOOSE
Background Pony #A494
full
Background Pony #DEB3
gotta fucking choose joHN OMG YES
Background Pony #D2CC
Ok, we HAD a consistant theme going until we reached Sonic. Someone care to tell me who f*** this all up?