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Description
Note: These picks are all entirely my opinion and I could very well be wrong on some of them, but what the heck.
Matchups in counter-clockwise order starting with:

Atom: Ant-Man VS Atom
Probably the one that needs the smallest amount of explaining, that being none at all.

Swords: Chosen Undead VS Dragonborn
It just seems like too fitting a choice given who we're talking about.

Le' Epic Beaker: Bowser VS Dr. Eggman
There's admittedly plenty of matchups it could be, including ones that we've gotten already, but this still feels like the most fitting choice for it. Not only does it represent them both (The beaker itself being Eggman's scientist nature / The spiked ball likely being Bowser's shell), but it's a matchup we're all expecting to see and both franchises are knocking it out of the park this year, Mario especially, so it just feels right.

Pentagram: Killua VS Misaka
I can't say much here given my lack of experience with these two franchises (I only know about Marvel and DC, after all), I hear this is a prominent symbol for them both, Killua in particular, so sure, this one checks out.

Suit: Kira VS Adachi
The symbol represents the sophisticated façade these two put up when they're not gleefully killing people, plus Jojosona is a rivalry that's been requested for the show for who knows how long.

Yin-Yang: Darth Vader VS Obito Uchiha
This symbol is all about balance of light and dark, which is a factor that these characters are well known for.

Half-Moon: Guts VS Dimitri
This one you could consider multi-layered. The moon part is symbolic because the Eclipse is what shaped Guts into who he is whereas Dimitri's story is called Azure Moon, plus the symbol being half-dark could show their dark side despite fighting evil and the fact that they're half-blind.

Scales: Cole MacGrath VS Alex Mercer
I'd consider this one interchangeable with Vader VS Obito's placement since it could mean the same thing given these two can be good or evil depending on what the player does with them.

Recycle: Phoenix VS Raven
It could represent Jean's constant cycle of death and rebirth, and the recycle aspect could relate to Raven being a returning character.

Star: Martian Manhunter VS Silver Surfer
They're aliens that travel through space. What more do you want?

Skull & Crossbones: Indiana Jones VS Jack Sparrow
The symbol itself is very much pirate-esque and it's not too unfitting for Indy given how many dangerous adventures he's gone on, plus we got a new Indiana Jones movie this year and a movie matchup this season would add a nice touch of variety.

Lotus: Liu Kang VS Jago
I dunno, whenever I see that symbol, I'm like "Oh, that's a symbol of being peaceful, which monks want to be, ergo I'm choosing this." That and it'd be nice to get a fighting game matchup this season, especially one that goes along with the new Mortal Kombat game coming out.

Dollar Sign: Scrooge McDuck VS Mr. Krabs
I know it'd be our third Disney matchup this season, but screw it, it fits too well.

Question Mark: Bill Cipher VS Discord
These two are chaotic as hell and will definitely keep us guessing what weird stuff they're gonna do to each other, so it's a good fit.

Shuffle: Ash Ketchum VS Yugi Muto
It goes along well with their fighting styles, both because Ash switches out his Pokemon for the right one all the time and because Yugi uses cards. I hear this one was deconfirmed, but until I know exactly what made that the case, I'm taking that statement with some salt.

Wave: Stitch VS Rocket Raccoon
This episode was very much the summer-themed one, with Stitch especially going along with it incredibly well and Rocket not falling too far behind there given the vibes of the music his buddy Quill likes.

Description
Note: These picks are all entirely my opinion and I could very well be wrong on some of them, but what the heck.
Matchups in counter-clockwise order starting with:

Atom: Ant-Man VS Atom
Probably the one that needs the smallest amount of explaining, that being none at all.

Swords: Chosen Undead VS Dragonborn
It just seems like too fitting a choice given who we're talking about.

Le' Epic Beaker: Bowser VS Dr. Eggman
There's admittedly plenty of matchups it could be, including ones that we've gotten already, but this still feels like the most fitting choice for it. Not only does it represent them both (The beaker itself being Eggman's scientist nature / The spiked ball likely being Bowser's shell), but it's a matchup we're all expecting to see and both franchises are knocking it out of the park this year, Mario especially, so it just feels right.

Pentagram: Killua VS Misaka
I can't say much here given my lack of experience with these two franchises (I only know about Marvel and DC, after all), I hear this is a prominent symbol for them both, Killua in particular, so sure, this one checks out.

Suit: Kira VS Adachi
The symbol represents the sophisticated façade these two put up when they're not gleefully killing people, plus Jojosona is a rivalry that's been requested for the show for who knows how long.

Yin-Yang: Darth Vader VS Obito Uchiha
This symbol is all about balance of light and dark, which is a factor that these characters are well known for.

Half-Moon: Guts VS Dimitri
This one you could consider multi-layered. The moon part is symbolic because the Eclipse is what shaped Guts into who he is whereas Dimitri's story is called Azure Moon, plus the symbol being half-dark could show their dark side despite fighting evil and the fact that they're half-blind.

Scales: Cole MacGrath VS Alex Mercer
I'd consider this one interchangeable with Vader VS Obito's placement since it could mean the same thing given these two can be good or evil depending on what the player does with them.

Recycle: Phoenix VS Raven
It could represent Jean's constant cycle of death and rebirth, and the recycle aspect could relate to Raven being a returning character.

Star: Martian Manhunter VS Silver Surfer
They're aliens that travel through space. What more do you want?

Skull & Crossbones: Indiana Jones VS Jack Sparrow
The symbol itself is very much pirate-esque and it's not too unfitting for Indy given how many dangerous adventures he's gone on, plus we got a new Indiana Jones movie this year and a movie matchup this season would add a nice touch of variety.

Lotus: Liu Kang VS Jago
I dunno, whenever I see that symbol, I'm like "Oh, that's a symbol of being peaceful, which monks want to be, ergo I'm choosing this." That and it'd be nice to get a fighting game matchup this season, especially one that goes along with the new Mortal Kombat game coming out.

Dollar Sign: Scrooge McDuck VS Mr. Krabs
I know it'd be our third Disney matchup this season, but screw it, it fits too well.

Question Mark: Bill Cipher VS Discord
These two are chaotic as hell and will definitely keep us guessing what weird stuff they're gonna do to each other, so it's a good fit.

Shuffle: Ash Ketchum VS Yugi Muto
It goes along well with their fighting styles, both because Ash switches out his Pokemon for the right one all the time and because Yugi uses cards. I hear this one was deconfirmed, but until I know exactly what made that the case, I'm taking that statement with some salt.

Wave: Stitch VS Rocket Raccoon
This episode was very much the summer-themed one, with Stitch especially going along with it incredibly well and Rocket not falling too far behind there given the vibes of the music his buddy Quill likes.