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Description
Figured I'd try this again given Discordant Decipher let us know which symbols were and weren't used, which made me rethink what to add.
Matchups in counter-clockwise order, starting with:

Atom: Ant-Man VS Atom
Again, I think you can all connect the dots for this one.

Swords: Chosen Undead VS Dragonborn
This one's also pretty obvious, even if they don't just use swords in battle.

Beaker: Bowser VS Dr. Eggman
Pairing how it fits 'em both (The beaker itself: Eggman being a scientist / The spikes: Bowser's shell) with how this symbol wasn't used yet and it's one of the most requested matchups to date, I see this as the best fit here. Also, most wanted matchup bias.

Pentagram: Ghost Rider VS Spawn
This one was a toss-up between this, Nero VS Hellboy, and Constantine VS Raidou, but given how iconic this matchup is on top of Spawn being one of the most requested returners out there, I can see it lining up.

Suit: Kira VS Adachi
The symbol could showcase their fashion sense and the sophisticated façade they have when they're not killing others, plus Jojosona is a well-known rivalry that surprisingly hasn't made it on the show yet.

Yin-Yang: Darth Vader VS Obito Uchiha
The symbol itself is all about balance between light and darkness, which is something these two are very familiar with.

Half-Moon: Guts VS Dimitri
The moon part works due to the Eclipse being a crucial part of Guts' story and Dimitri's route being called Azure Moon, and the lighting works due to their dark side despite fighting evil and their half-blindness.

Scales: Cole MacGrath VS Alex Mercer
Similar to Vader VS Obito, this could represent how these two can walk the path between good and / or evil depending on what the player does.

Recycle: Aang VS Captain Planet
The symbol itself perfectly lines up with Captain Planet's message about taking care of the planet whereas Aang fights using the planet's elements, not to mention Chad has wanted a Captain Planet episode ever since Aang had one.

Star: Martian Manhunter VS Silver Surfer
This one was an easy one given who we're talking about, especially since we know this symbol was used.

Skull & Crossbones: Indiana Jones VS Jack Sparrow
The symbol itself is unmistakably pirate-based, and it's a decent fit for Jones too given the dangerous adventures he goes on, with his recently-released movie likely helping this matchup's chances.

Lotus: Phoenix VS Raven
The lotus is a symbol of purity and rebirth, and I'm sure you can guess how that connects to these two.

Dollar Sign: Killua VS Misaka
We know that this symbol was used already, and given Killua's rich while Misaka fights with coins, it's definitely the best fit out of what we've got.

Question Mark: Bill Cipher VS Discord
I'm sure this one goes without saying given their chaotic and random nature.

Shuffle: Jack Skellington VS The Grinch
Okay, hear me out on this one. Apparently, that symbol is specifically a music shuffle, which could mean it's a matchup that features two characters known for music. I was tempted to put Brook VS Lord Raptor here, but given this one lines up pretty well too (What with Jack singing all the time, the iconic "This is Halloween" song, and singing being what helped the Grinch's heart grow three sizes), plus we have yet to have a Christmas-themed matchup on the show, I can see it being this one.

Wave: Stitch VS Rocket Raccoon
You could probably interchange this placement with Manhunter VS Surfer, but given this was the season's summer-themed episode, I think it lines up well.

Description
Figured I'd try this again given Discordant Decipher let us know which symbols were and weren't used, which made me rethink what to add.
Matchups in counter-clockwise order, starting with:

Atom: Ant-Man VS Atom
Again, I think you can all connect the dots for this one.

Swords: Chosen Undead VS Dragonborn
This one's also pretty obvious, even if they don't just use swords in battle.

Beaker: Bowser VS Dr. Eggman
Pairing how it fits 'em both (The beaker itself: Eggman being a scientist / The spikes: Bowser's shell) with how this symbol wasn't used yet and it's one of the most requested matchups to date, I see this as the best fit here. Also, most wanted matchup bias.

Pentagram: Ghost Rider VS Spawn
This one was a toss-up between this, Nero VS Hellboy, and Constantine VS Raidou, but given how iconic this matchup is on top of Spawn being one of the most requested returners out there, I can see it lining up.

Suit: Kira VS Adachi
The symbol could showcase their fashion sense and the sophisticated façade they have when they're not killing others, plus Jojosona is a well-known rivalry that surprisingly hasn't made it on the show yet.

Yin-Yang: Darth Vader VS Obito Uchiha
The symbol itself is all about balance between light and darkness, which is something these two are very familiar with.

Half-Moon: Guts VS Dimitri
The moon part works due to the Eclipse being a crucial part of Guts' story and Dimitri's route being called Azure Moon, and the lighting works due to their dark side despite fighting evil and their half-blindness.

Scales: Cole MacGrath VS Alex Mercer
Similar to Vader VS Obito, this could represent how these two can walk the path between good and / or evil depending on what the player does.

Recycle: Aang VS Captain Planet
The symbol itself perfectly lines up with Captain Planet's message about taking care of the planet whereas Aang fights using the planet's elements, not to mention Chad has wanted a Captain Planet episode ever since Aang had one.

Star: Martian Manhunter VS Silver Surfer
This one was an easy one given who we're talking about, especially since we know this symbol was used.

Skull & Crossbones: Indiana Jones VS Jack Sparrow
The symbol itself is unmistakably pirate-based, and it's a decent fit for Jones too given the dangerous adventures he goes on, with his recently-released movie likely helping this matchup's chances.

Lotus: Phoenix VS Raven
The lotus is a symbol of purity and rebirth, and I'm sure you can guess how that connects to these two.

Dollar Sign: Killua VS Misaka
We know that this symbol was used already, and given Killua's rich while Misaka fights with coins, it's definitely the best fit out of what we've got.

Question Mark: Bill Cipher VS Discord
I'm sure this one goes without saying given their chaotic and random nature.

Shuffle: Jack Skellington VS The Grinch
Okay, hear me out on this one. Apparently, that symbol is specifically a music shuffle, which could mean it's a matchup that features two characters known for music. I was tempted to put Brook VS Lord Raptor here, but given this one lines up pretty well too (What with Jack singing all the time, the iconic "This is Halloween" song, and singing being what helped the Grinch's heart grow three sizes), plus we have yet to have a Christmas-themed matchup on the show, I can see it being this one.

Wave: Stitch VS Rocket Raccoon
You could probably interchange this placement with Manhunter VS Surfer, but given this was the season's summer-themed episode, I think it lines up well.