Tōshirō Hitsugaya vs. Luppi Antenor

Tōshirō Hitsugaya vs. Luppi Antenor is a fight that occurred during the Arrancar Invasion and located in Karakura Town between Captain Tōshirō Hitsugaya of the 10th Division and 6th Espada, Luppi Antenor.

Prelude
Sōsuke Aizen sends four powerful Arrancar to Karakura Town to create a distraction that will allow the abduction of Orihime Inoue. They immediately encounter Hitsugaya and his front guard in the Karakura Park. Hitsugaya initially confronts Yammy Llargo, who introduces himself as the 10th Espada. Luppi begins an altercation with Yumichika Ayasegawa and reveals himself to be the sixth Espada. Yumichika takes a beating against Luppi until the latter asks Ikkaku Madarame if he intends to step in, to which Ikkaku replies that he won't fight two on one. Luppi contemplates the situation and then informs everyone that he intends to release his Zanpakutō and take on Hitsugaya, Yumichika, Ikkaku and Lieutenant Rangiku Matsumoto in a one on four match.

Battle
Hitsugaya, remembering his fight with Shawlong Koufang, attempts to halt Luppi immediately by using his Bankai, Daiguren Hyōrinmaru. However, his response is too slow as Luppi manages to use his Resurrección, Trepadora to counter. He immediately attacks the captain with a long extending tentacle, which Hitsugaya blocks with his ice wings. Hitsugaya is initially dismissive of the Resurrección's strength, but as the smoke clears away, the true shape of Trepadora is revealed to be eight enormous tentacles connected to Luppi at one of the corners of an octagonal design on his back, with a bone cowl growing over Luppi's head. Luppi attacks Hitsugaya with seven vines at once and manages to land a hit, throwing the captain away from the battlefield. Luppi then boasts to the lower ranking Shinigami present that their match is supposed to be four-on-one, but corrects himself and says that it is "eight-on-four."

As their match goes on, the trio are finding themselves struggling against Luppi. Luppi soon gets bored with beating Gotei 13 seated officers and seizes each of them with his tentacles. Luppi comments on Rangiku's body and then asks her if he should "fill it with holes" with the spikes on his tentacle. Rangiku braces for impact, but she is saved by the timely arrival of Kisuke Urahara, who cuts the tentacle with Benihime's energy blast. Luppi then asks who he is, to which Urahara introduces himself

As Urahara battles again Wonderweiss Margela and Yammy, Luppi watches on. He comments on how he thought that he would get to kill Urahara since he had disrupted his attack, annoyed that Yammy took him. He quickly dismisses it, thinking that Urahara would die regardless if it was by him or Yammy and turns his attention back to his intended victims. The Espada then taunts the three Shinigami. Rangiku manages to stall him by commenting on his excessive chattering. The ploy works as Hitsugaya returns to the battlefield and begins to freeze Luppi's tentacles just as he is about to finish his retort. The captain informs Luppi that he is too lenient and asks if he ever heard of Zanshin (not letting up on one's opponent even if they seem beaten). Luppi is completely surprised that Hitsugaya was still alive to which Hitsugaya simply comments that Hyōrinmaru will reform as it is the strongest ice & snow type Zanpakutō. Luppi moves to make an attack, but is told to stop as he has no chance of winning because he had given Hitsugaya too much time to prepare. Hitsugaya then remarks that if Luppi has eight arms for a weapon, Hitsugaya has all the water in the atmosphere as his. The captain then proceeds to use Sennen Hyōrō on the Espada, encasing him in ice. Hitsugaya plainly remarks that eight arms were simply not enough

Luppi remains encased in Hitsugaya's technique until the mission for which he and his comrades were sent to Karakura is achieved, upon which a ray of Negación engulfs Luppi and destroys the Sennen Hyōrō. Luppi departs with a promise to crush Hitsugaya's head the next time they meet.

Aftermath
Tōshirō returns, along with the rest of his group, to the Urahara Shop. Having witnessed the Arrancar's strength, he becomes concerned with the Gotei 13's state of preparedness and is determined to push for a speed up of preparations.