Tōshirō Hitsugaya vs. Luppi Antenor

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Concurrent	Good Bye Halcyon Days Kisuke Urahara vs. Yammy Llargo Ichigo Kurosaki vs. Grimmjow Jaegerjaquez: Rematch
Next	Enter The Home of Hollows
Tōshirō Hitsugaya vs. Luppi Antenor
Conflict	Arrancar Invasion
Date	October 29th, 2001
Place	Human World, Karakura Town
Outcome	Draw, Luppi Antenor escapes via Negación.
Combatants
Captain Tōshirō Hitsugaya Support: Lieutenant Rangiku Matsumoto 3rd Seat Ikkaku Madarame 5th Seat Yumichika Ayasegawa
Captain Tōshirō Hitsugaya Support: Lieutenant Rangiku Matsumoto 3rd Seat Ikkaku Madarame 5th Seat Yumichika Ayasegawa
6th Espada Luppi Antenor
6th Espada Luppi Antenor
Powers & Abilities
Zanjutsu Zanpakutō (Shikai, Bankai) Sennen Hyōrō
Zanjutsu Zanpakutō (Shikai, Bankai) Sennen Hyōrō
Zanpakutō (Resurrección) Lanza Tentáculo Jaula Tentáculo La Hélice Hierro Virgen
Zanpakutō (Resurrección) Lanza Tentáculo Jaula Tentáculo La Hélice Hierro Virgen
Damage Sustained/Casualties
Hitsugaya is moderately wounded.
Hitsugaya is moderately wounded.
Luppi is moderately wounded.
Luppi is moderately wounded.

Tōshirō Hitsugaya vs. Luppi Antenor is a fight taking place during the Arrancar Invasion between 10th Division Captain Tōshirō Hitsugaya and Espada #6. Luppi Antenor.

Prelude

Luppi Antenor attends the Arrancarification ceremony of Wonderweiss Margela.

In Las Noches, Luppi Antenor attends the Arrancarification ceremony of Wonderweiss Margela alongside Coyote Starrk, Tier Harribel, Ulquiorra Cifer, Nnoitra Gilga, Grimmjow Jaegerjaquez, and Yammy Llargo, where Sōsuke Aizen temporarily fully awakens the Hōgyoku by briefly fusing with it in order to create Wonderweiss. Once this is done, Aizen reminds Ulquiorra of the order they discussed a month prior and instructs him to carry it out while taking anyone he wishes along with him, with Ulquiorra selecting Luppi among several others.

Tōshirō Hitsugaya and Ikkaku Madarame perform Jinzen in Karakura Town.

Meanwhile, in Karakura Town, 10th Division Lieutenant Rangiku Matsumoto and 11th Division 5th Seat Yumichika Ayasegawa begin fighting while attempting to perform Jinzen, which prompts 10th Division Captain Tōshirō Hitsugaya to threaten to send them back to Soul Society if they do not shut up and concentrate prior to lamenting their inability to communicate with their Zanpakutō Spirits more quietly while performing Jinzen with his own Zanpakutō next to 11th Division 3rd Seat Ikkaku Madarame, who opens his eyes to notice that the clouds are moving quickly in the sky above them, though he denies having said anything when Hitsugaya notices his reaction.

Luppi, Yammy Llargo, Grimmjow Jaegerjaquez, and Wonderweiss Margela appear.

Suddenly, a Garganta rips open in the sky, alerting Hitsugaya, Rangiku, Ikkaku, and Yumichika, to reveal Luppi, Yammy, Grimmjow, and Wonderweiss standing within. On the ground below, Yumichika is stunned by the Arrancar showing up earlier than expected, though Hitsugaya observes that there is no time to figure out why they have done so, as Yammy notes that they picked a good spot because there are combatants with strong Reiatsu below them. In turn, Luppi notes that these are Shinigami and likely the reinforcements from Soul Society that the sixth Espada told them about, but snidely corrects himself and addresses Grimmjow as the former sixth Espada after turning to him. However, Grimmjow simply asserts that the man he wants to kill is not down there and leaps away from the Garganta, startling Yammy, who is told by Luppi to let Grimmjow go since the latter is worthless now that he has had his tattoo burned off and is no longer an Espada.

Hitsugaya suddenly attacks Yammy with Hyōrinmaru.

When Yammy realizes that the one he wants to kill is not down there either, Luppi inquires about whether he is referring to the one who cut off his arm, the one who beat him up, or the one who deflected his Cero, prompting a grinning Yammy to declare that he is referring to all of them prior to telling Wonderweiss that it is time to go and berating him for just standing there and drooling, only for Wonderweiss to not respond and continue staring into space, to Yammy's disappointment. Suddenly, Hitsugaya attacks Yammy in a flurry of ice, forcing Yammy to partially draw his Zanpakutō in order to defend himself against the slash, and introduces himself, which leads Yammy to comment on the coincidence since he is Arrancar #10. Upon being identified as an Espada by Hitsugaya, Yammy observes that he must have fought someone who likes to talk if he knows about them.

Finding Ikkaku and Yumichika Ayasegawa to be boring, Luppi decides to fight all four of the present Shinigami at once with his Resurrección.

Nearby, Luppi confronts Ikkaku and Yumichika, and when the latter inquires if he is an Espada too, Luppi confirms this and reveals a tattoo of the number 6 on his right hip. Shortly afterward, Yammy shatters the ice encasing him and mockingly calls it refreshingly cool while Hitsugaya internally realizes that he will have to use his Bankai against Yammy even with the Gentei Kaijo leaving his power unrestricted. Simultaneously, Yumichika is sent flying by a blow from Luppi, who reiterates that Yumichika cannot beat him alone. Bleeding from a wound on his left temple, Yumichika simply tells Luppi to shut up, prompting the latter to ask Ikkaku if he will talk to Yumichika or let the latter die out of exasperation, only for Ikkaku to note that two against one is not his style. Annoyed by this, Luppi asks Yammy to let him have Hitsugaya so he can take Ikkaku, Yumichika, Hitsugaya, and Rangiku on all at once with his Resurrección, since he considers them too weak to fight individually.

Battle

Luppi activates his Resurrección, Trepadora.

Upon seeing Luppi drawing his Zanpakutō, Hitsugaya recalls Shawlong Koufang doing this and refuses to let Luppi do the same as he rushes toward the latter and activates his Bankai, Daiguren Hyōrinmaru. However, a smirking Luppi manages to activate his Resurrección, Trepadora, releasing a huge cloud of steam that envelops Hitsugaya. Suddenly, a thick tentacle hurtles out of the steam and slams into Hitsugaya, who barely blocks it with his left ice wing and is sent skidding back through the air. Though Hitsugaya comes to a halt and questions if this is the extent of Luppi's Resurrección attack, Luppi simply praises him for being able to stop the attack against expectations and admits that the captains are decent, only to inquire about what Hitsugaya would do if this attack were eight times stronger while the steam clears to reveal seven more identical tentacles attached alongside the first one to a large protrusion on his back. With Hitsugaya stunned by this, Luppi attacks him with Jaula Tentáculo, slamming all eight tentacles into Hitsugaya simultaneously from different angles in an explosion of force. As Rangiku frantically calls out to a cursing Hitsugaya, who falls out of the air, Luppi reminds the Shinigami that he told them to fight him four-on-one, only to snidely correct himself and describe this as four-on-eight.

Kisuke Urahara saves Rangiku from Luppi.

Soon afterward, Luppi uses La Hélice to rapidly spin the tentacles on his back and strike Rangiku, Ikkaku, and Yumichika multiple times with them, leaving the Shinigami bleeding. Unimpressed by this, Luppi questions if they are really officers of the Gotei 13 and continues attack them in boredom. Upon succeeding in binding Rangiku, Ikkaku, and Yumichika with his tentacles, Luppi compliments Rangiku for having such a curvaceous body, but threatens to puncture it with many holes as he uses Hierro Virgen to sprout dozens of spikes from the tip of the tentacle restraining Rangiku, who grimaces upon seeing it hurtle toward her. Suddenly, the tentacle is severed by Kamisori, Benihime, freeing Rangiku and shocking Luppi, and Kisuke Urahara expresses relief at arriving just in time.

Luppi restrains Rangiku, Ikkaku, and Yumichika.

When an annoyed Luppi questions who he is, Urahara apologizes for not introducing himself and explains that he runs a candy store called the Urahara Shop as he claims that it is delightful to make Luppi's acquaintance and prepares to attack, only to be interrupted by Wonderweiss. With Yammy seemingly overwhelming Urahara with several Bala blasts afterward, Luppi sighs at Yammy having likely already killed Urahara even though he wanted to do so himself and turns his attention back to Rangiku, Ikkaku, and Yumichika, who are still wrapped up in his tentacles.

Luppi discovers that his bottom four tentacles have suddenly been frozen.

Luppi questions the logic of Urahara showing up to save the day and getting himself killed so quickly, only to admit that there is nowhere for them to run while outnumbered eight to three anyway. In response, an unamused Rangiku points out how much Luppi talks and asserts that braggarts like him make her sick, prompting an irritated Luppi to remind Rangiku that her life is in his hands due to his tentacle being wrapped around her and vow to perforate her if she makes him mad. However, when Luppi attempts to bring his remaining four tentacles up, he is astonished to discover that they have been frozen to the ground below as Hitsugaya rises up with Daiguren Hyōrinmaru still activated and criticizes Luppi for being careless enough to drop his guard and ignore his opponent. When Luppi expresses disbelief at him still being alive, Hitsugaya asserts that Daiguren Hyōrinmaru is the ultimate ice weapon.

Hitsugaya encases Luppi in ice with Sennen Hyōrō.

When Hitsugaya explains that this means it will always reform so long as water is nearby no matter how many times it is shattered, an unnerved Luppi frantically attempts to attack him. However, Hitsugaya informs him that there is no point in doing so since Luppi's negligence gave him more than enough time to prepare and reveals that Luppi's weapon having eight arms is outclassed by his own having all the water in the atmosphere while dozens of large ice pillars appear in the surrounding air to encircle him and Luppi. After encasing a shocked Luppi in the rapidly converging ice pillars with Sennen Hyōrō, Hitsugaya observes that eight arms was not quite enough for him.

Aftermath

A Negación beam saves Luppi by extracting him from the ice prison.

Some time later, once Ulquiorra completes his own mission and begins extracting his team, Luppi is freed from Sennen Hyōrō by a Negación beam and sarcastically apologizes about Hitsugaya being unable to kill him before promising to twist the latter's head off and crush it next time they meet. That evening, as he recovers in Urahara's Study Chamber, Hitsugaya ruminates on how they got off easy considering the number of Espada who came to Karakura Town and how the Gotei 13 made a grave miscalculation due to the Arrancar being fully operational and ready to battle, concluding that they have to prepare for battle immediately.