Bleach is one of the most popular manga of all time, forming a part of the Big Three along with Naruto and One Piece. The other two series received cohesive anime adaptations of their own that haven't taken a major break, with One Piece still going strong weekly to this day. However, Bleach ended abruptly after the Fullbring arc following weak manga sales and anime viewership. Still, it seems that Bleach: Thousand-Year Blood War is poised to change things quite a bit.
Now's a great time to take a look at Ichigo and his history of battles throughout the series. While he's had his fair share of victories, Ichigo has also dealt with several losses that are worth a mention too. Keeping this in mind, here are some of Ichigo's biggest defeats in Bleach.
Special Mention: VS Kageroza Inaba
The quality of filler in Bleach varies quite a bit, but most people consider the Reigai Uprising to be worth a watch. One of the battles in this arc is pretty great, with Ichigo, Yamamoto & Nozomi battling against the arc's antagonist, Kageroza Inaba. The battle is a grueling one, and leads to Ichigo losing his powers after being slashed across the chest by Kageroza.
5 Byakuya Kuchiki & Renji Abarai
After becoming a Substitute Shinigami, Ichigo pulls his weight and ends up being competent in this role. However, nothing could have prepared him for the might of an actual Shinigami. He gets to witness this firsthand when Byakuya and Renji come to Earth to take Rukia back to Soul Society for her trial and execution.
This causes Ichigo to fly into a rage, clashing blades with Renji in the process. However, it's Byakuya who shows him the discrepancy in their powers. He wastes no time in slashing Ichigo and showing him just how powerless he really is. It was a great way to set up their future conflict, with the Soul Society arc easily being the best part of Bleach.
4 Ulquiorra Cifer
Ulquiorra is one of the most interesting antagonists during the Arrancar arc. He personally takes Orihime back to Hueco Mundo, prompting a rescue mission where Ichigo and his friends break into the domain of the Arrancar in a bid to save Orihime and take Aizen out in the process.
However, Ulquiorra's appearance makes it clear that Ichigo is nowhere near ready to deal with the threat of the Arrancar. After attaining a ton of power-ups, Ichigo tries to take on Ulquiorra...only to realize how hopelessly outmatched he is. His most powerful attacks do nothing against Ulquiorra, who humiliates Ichigo and pierces the protagonist's chest with his hand before walking away.
3 Gin Ichimaru
Gin Ichimaru is a pretty fascinating character in Bleach, initially appearing as nothing more than a dastardly antagonist who teams up with Aizen for his own nefarious purposes. However, before this revelation is made, it's only a given that Gin had to maintain appearances to avoid drawing the suspicion and ire of Aizen. This leads to a fight with Ichigo, where he shows the young upstart just how weak he really is, even after all the training he's done.
Gin absolutely schools Ichigo, meticulously explaining to him the powers of his Zanpakuto before dismantling Ichigo with a wide variety of techniques. Even the use of a Hollow Mask isn't enough to make any sort of mark on Gin, who berates Ichigo and wears him down mentally by asking him a ton of tough questions that Ichigo can't answer. He shows his good side briefly after telling Ichigo to leave the battlefield, constructing it like a veiled threat when he is actually trying to prevent Ichigo from being killed by Aizen prematurely.
2 Shukuro Tsukishima & Xcution
After losing his Shinigami powers in his final fight against Aizen, Ichigo gets bored with the peaceful life. This prompts him to try and find a way of helping people out once again. This leads to the protagonist seeking out Xcution and getting Fullbring powers of his own. However, Kugo Jingo tells him that Tsukishima has betrayed Xcution, prompting him to go face off against this supposed traitor...only to see that Tsukishima had rewritten the memories of his family and friends.
This leads to a battle where Ichigo ends up fighting against both friends and foes. As the battle goes on, Kugo reveals his true intentions at the end and stabs Ichigo, stealing his Fullbring powers in the process. This turns Ichigo powerless once again — although not for long, since the Shinigami of Soul Society came back to give Ichigo his powers back and help out in this fight against Xcution.
1 Yhwach
While this fight has technically not happened in the anime yet, most people know about the power of Yhwach and just how devastating he can be. After all, this man managed to kill the Captain-Commander of the Gotei 13, the great Genryusai Yamamoto himself. Even with all the power-ups in the world, Ichigo was bound to have a tough time with the son of the Soul King.
However, the sheer disrespect in the final fight against Yhwach was genuinely immense. Not only was Ichigo's Bankai broken, but all his attempts to kill Yhwach were either thwarted or reversed by the Almighty's powers. This led to Ichigo losing his will to fight, and it was only after his friends came to give him a helping hand that Ichigo mustered the courage to fight against Yhwach a second time.