The Third Siege of Odawara in 1590 was a pivotal moment in Toyotomi Hideyoshi's efforts to neutralize the Hojo clan as a challenge to his authority. In the months leading up to the siege, the Hojo made significant, hurried improvements to the castle's defenses as Hideyoshi’s intentions became clear. However, despite Hideyoshi's overwhelming force, there was little actual combat during the siege.
By 1588, Toyotomi Hideyoshi had largely unified Japan, following several military campaigns after the death of Oda Nobunaga in 1582. He requested that Hojo Ujimasa and his son Ujinao visit him in Kyoto at his residence, Jurakudai, but Ujimasa refused, suggesting a later visit in 1590. Hideyoshi rejected this delay, worsening relations between the two. In May 1590, Hideyoshi launched the Odawara Campaign against the Hojo.
Ujimasa hoped for support from Date Masamune or even a defection by Tokugawa Ieyasu if the conflict dragged on. Hideyoshi's massive army encircled Odawara Castle in what is often described as "the most unconventional siege in samurai history." The besieging forces were entertained by performers—concubines, musicians, acrobats, and more—while the defenders, though outnumbered, maintained their positions on the ramparts, armed with arquebuses. As a result, Hideyoshi refrained from launching a full attack, relying instead on traditional starvation tactics. Only a few small skirmishes occurred, such as when miners from Kai Province tunneled under the walls, allowing forces led by Ii Naomasa to breach the castle.
After three months, the sudden construction of Ishigakiyama Ichiya Castle near Odawara crushed the Hojo’s morale, leading to their surrender. In addition to taking Odawara Castle, Hideyoshi's forces, led by Maeda Toshiie and Uesugi Kagekatsu, captured several Hojo strongholds, including Matsuida, Minowa, Maebashi, Matsuyama, Hachigata, and Hachioji Castles. His navy, under Chosokabe Motochika, also defeated the Izu suigun at Shimoda Fortress in Ise Province.
During the campaign, the Chiba clan, allies of the Hojo in Shimosa, saw their Sakura Castle fall to Honda Tadakatsu and Sakai Ietsugu of Tokugawa’s forces. Chiba Shigetane, the clan’s daimyo, surrendered on the condition that his family would not be abolished. While the Chiba lost all their holdings, many of their senior members were later taken into service by Tokugawa’s retainer, Ii Naomasa, as a gesture of gratitude for earlier aid.
At Oshi Castle, led by Ishida Mitsunari, the defenders surrendered upon hearing of the Hojo’s defeat at Odawara. Hojo Ujimasa was unable to defend Odawara against Hideyoshi's forces, and the castle fell. Ujimasa and his brother Ujiteru were both forced to commit seppuku.
Following the campaign, Hideyoshi rewarded Tokugawa Ieyasu with the Hojo lands, not knowing that this would eventually position Ieyasu to become shogun. The siege also saw the tragic end of the tea master Yamanoue Soji, who was in the service of the Hojo lords and was sentenced to death by torture after the fall of Odawara.
See also
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The Siege of Inabayama Castle
The two-week-long siege of Inabayama Castle marked the dramatic climax of Oda Nobunaga’s campaign to assert control over Mino Province and decisively crush the Saitō clan. It was during this operation that Toyotomi Hideyoshi, then known as Kinoshita Tōkichirō, first shone brightly in competition with Nobunaga—emerging as the future heir to Japan’s unification.
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The Siege of Wado Castle
In 1335, the Shiina clan built Uozu Castle as an auxiliary stronghold supporting Matsukura Castle. By 1570, it had fallen under the control of the Uesugi clan, rapidly emerging as a strategic fortress in Etchū Province. For many years, Kawada Nagataka served as its commander.
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The siege of the Ishimama Honganji monastery
In Japanese history, the siege of Ishiyama Hongan-ji — the main stronghold of the Ikkō-ikki movement during Oda Nobunaga’s campaign — is considered the longest, lasting from August 1570 to August 1580.
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The Battle of Norada
The Battle of Norada is a striking example of a clash during the Sengoku Jidai period, when numerical superiority did not always guarantee victory, even in open battle.
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Battles of Kawanakajima
The Battles of Kawanakajima were a series of fierce conflicts during Japan's Sengoku period, waged between Takeda Shingen of Kai Province and Uesugi Kenshin of Echigo Province from 1553 to 1564. These battles centered around the strategic Kawanakajima plain, lying between the Sai and Chikuma rivers in northern Shinano Province, now within Nagano City. The rivalry began when Shingen took control of Shinano, forcing Ogasawara Nagatoki and Murakami Yoshikiyo to seek refuge with Kenshin, prompting repeated clashes.
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Battle of Tenmokuzan
The Battle of Tenmokuzan in 1582 is remembered as the final stand of the Takeda clan in Japan. This battle marked the last attempt by Takeda Katsuyori to resist Oda Nobunaga's relentless campaign against him. Fleeing from his pursuers, Katsuyori set fire to his fortress at Shinpu Castle and sought refuge in the mountains at Iwadono, a stronghold held by his loyal retainer, Oyamada Nobushige. However, Oyamada betrayed Katsuyori, denying him entry. Left with no other option, Katsuyori committed suicide alongside his wife, while the remnants of his army made a valiant effort to hold off their attackers.
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Battle of Oshu
The Northern Fujiwara clan had governed the Mutsu and Dewa provinces since 1087, maintaining their rule for over a century by 1189. The clan was founded by Fujiwara no Kiyohira, alongside Minamoto no Yoshiie, who established their independence in Hiraizumi, located in present-day Iwate Prefecture. Under Kiyohira, and later his successors Fujiwara no Motohira and Fujiwara no Hidehira, the Northern Fujiwara reached the height of their power in the Tohoku region. They infused the area with Kyoto culture and constructed significant temples, such as Chuson-ji, founded in 1095.
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Battle of Omosu
The 1580 Battle of Omosu (Omosu no Tatakai) was one of many conflicts between the Hojo and Takeda clans during Japan's Sengoku period. What sets this battle apart is its rarity as one of the few naval engagements in pre-modern Japan. The conflict occurred off the coast of the Izu Peninsula, involving the fleets of Hojo Ujimasa, the leader of the Hojo clan, and Takeda Katsuyori, the head of the Takeda clan.
