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vs


Both 7-A
Speed =
SBA otherwise
 
Itachi just kinda Genjutsu GG's tbh.

Issei doesn't resist layered Mind Manipulation and Illusion Creation, nor can he effectively nullify the Genjutsu with anything else. I guess someone could make the argument that Vanishing Dragon could divide Itachi's out-putted chakra to the point it vanishes, but I just don't see Issei being capable of doing that before he gets slapped up by Itachi.
 
Which Volume of DxD is the Issei you are you using here? Double checking the wiki, everything up to Cardinal Crimson is under 7-A, though later volumes bump that particular mode up. Even then, that leaves his regular BxB and Triana.

Regardless, in a speed equalized match, Itachi would win due to genjutsu. Otherwise, Issei can blitz him and win rather handily, with the in-series match of Issei vs Kuisha Abaddon being a good example of what would happen.
 
Which Volume of DxD is the Issei you are you using here? Double checking the wiki, everything up to Cardinal Crimson is under 7-A, though later volumes bump that particular mode up. Even then, that leaves his regular BxB and Triana.

Regardless, in a speed equalized match, Itachi would win due to genjutsu. Otherwise, Issei can blitz him and win rather handily, with the in-series match of Issei vs Kuisha Abaddon being a good example of what would happen.
SBA assumes strongest 7-A version of issei
are you sure issei can blitz out before itachi uses genjutsu
 
SBA assumes strongest 7-A version of issei
are you sure issei can blitz out before itachi uses genjutsu
Then that's Illegal Move Triaina or the initial activation of Cardinal Crimson Promotion.

I found a clip of the battle I referenced (Issei vs Kuisha), though it took forever because it was a small scene before the big fight of the season.



The fight starts at 8:54 and ends at 9:12 though most of that was the two combatants talking to each other. The reactions of other characters continues up to 9:20.

Kuisha is a spellcaster/ranged attacker primarily, so she'd fit in the Itachi spot. Note the moment the battle officially started, she was taken out.

I also have the lines about it from Volume 10, with this particular scene being from the PoV of Rias Gremory. I'll note this was from the fan translated version as I haven't received the official English version of Volume 10 yet, but so far the official English translations of DxD haven't deviated all that much from the fan translations.
It seems like Abaddon seems to be suspicious at Ise talking to himself……

[The seventh match! Begin now!]

The signal was given! Abaddon didn’t do anything much and was waiting for Ise to move.

[Sekiryuutei, get into Balance Breaker. My master Sairaorg-sama wishes to see you become serious. Then I, his [Queen] have to make that wish come true.] She’s a woman with strong resolution. That person, she must have feelings for Sairaorg….. The countdown ended, and Ise said a single sentence to Abaddon after wearing his armour.

[……..I can’t hold back. If you don’t want to die, put all your strength into defending. If you do that, then you will be able to retire safely.]

[You sure talk big. Very well. I will also stop you with my full power. Whether it’s the Sekiryuutei, for master I will--]

[-I have warned you.]

Ise’s body gets enveloped by red lights….

[Welsh Sonicboost Knighhhhhhhhhht!]

[Change Star Sonic!!!!]

The armour gets purged, and Ise leaps forward in godspeed. In a velocity of godspeed, Ise arrives in front of Abaddon before she reacts. Even I couldn’t see him at all until he closed in! Ise then shouts while enveloping his body with red aura!

[Welsh Dragonic Roooooooook!]

[Change Solid Impact!!!!]

Ise’s armour became thicker.

[Uoooooooooooooooo!]

Ise who makes a loud shout. While having the percussion hammer on his shoulder ring, his punch gets faster while pouring out more aura. That strike without any hesitation goes at Abaddon…..

FLASH! Before that happens, Abaddon’s body gets covered in light and she disappears from the field! GOOOOOOOOOOOOOOOON! The strike which hits the air destroys the colosseum without a trace.

[Combatant Sairaorg Bael’s [Queen] retires.] The arbiter announces.

–It’s Ise’s victory. Everything ended instantly. He shortened the distance with Triaina, and he also tried to settle the match instantly as well. Abaddon didn’t even have time to make the ‘hole’ appear. But that strike didn’t hit her. Before it was about to hit the [Queen], it looked as if she was forced to retire by someone. No, she was forced to retire. –By her master Sairaorg.

Sairaorg appears on the monitor. He had a mortified expression.

[…………I made Kuisha retire forcefully. At that rate, she would have been killed by Sekiryuutei. You were trying to kill her, were you not?]
 
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