Hasedo Castle, one of the three southwestern castles that defended the Uesugi family, was defended by Shimura Izu Shoukoyasu, with a garrison of 5,000 men. From 18 February, Naoe Kanesuke deployed his main camp on Mt. Sugasawa in the northwest of the castle, and on the same day sent 900 Uesugi soldiers to advance along the foothills of Mt. Omori to the west and Hachimangasaki Pass to the north.

Under the repeated fire of the iron artillery, the Uesugi army approached Hasedo Castle step by step, and the defender Shimura Mitsuyasu ordered the iron artillery in the castle to return fire, and the two sides began to fire fiercely. The Uesugi army relied on the momentum to attack under Oteguchi, and the defenders of the castle swarmed out when they saw this, and the two armies engaged in white-knuckle battles in the streets and mud fields, and the battle of Hasedo Castle began, and the battle lasted until the evening, when the retainer of Mogami Shinseki was killed and the two sides were suspended.

On the same day, Sugawa, Kashiwakura, Hachimangu Shrine, and other places, the Uesugi army also launched an attack on the Mogami army's position. Due to the resistance of the Mogami Date coalition army, the Uesugi army could no longer expand the victory, and the two sides entered a stalemate, and the Uesugi army began to besiege Hasedo Castle, but the remaining Masakai refused to send troops into the city in order to preserve its strength, and was only willing to attack the outer Uesugi army in the Sugawa area.

On February 20, Naoe Kanesuke learned that Date Masamune had captured Shiraishi Castle, but Hasedo was still a fortified castle and stood in front of Yamagata Castle, so in order to more effectively besiege Hasedo, he sent Yokota Toshitoshi and Sebe Mitsucho to lead 5,000 troops to attack Kamiyama Castle south of Hasedo Castle, intending to capture the castle in order to contain Hasedo Castle.

Yokota Toshitoshi and Shibe Hikaraga approached Kamiyama Castle in two ways, and the general of Kamiyama Castle, Satomi, had already learned of the attack of the Uesugi army the day before, so he urgently summoned 1,500 defenders in the castle, and on the one hand, he took the initiative to meet Sebe Mitsunaga, and on the other hand, he joined the Kusakari Shima garrison sent by Mogami Yoshimitsu of Yamagata Castle and set up an ambush in the valley of Mt. Kagitori and Mt. Tenjin in the south of Kamiyama Castle.

At 10 a.m. on the morning of the 22nd, Mitsucho Sebe first reached the Kawaguchi area, which was only 5,000 meters away from Kamiyama Castle, and launched an attack on Mogami's army, and his general Naito Saemon gradually advanced and assembled in the Ishisone area, which was only 2,500 meters away from Kamiyama Castle. And Yokota's main army also crossed the Chungkawanuma and crossed the Muhuai area towards Akasaka, Fujigo, and Amitabha. As long as these three areas are occupied, the Uesugi army can suddenly appear behind the defenders of Mogami Ueyama and complete the surprise attack with a flank attack in front and back.

However. When he arrived at the passage between Mt. Kitori and Mt. Tenjin, the sound of iron cannons behind Yokota was repeated. The top ambush soldiers in the mountains and forests on both sides were instantly killed, and the Uesugi army was immediately encircled by the other side. In the melee, Yokota was captured by Shimamoru Kusakari, and the remnants of the Uesugi army retreated to Nakayama Castle.

The Uesugi army on the side of Kawaguchi and Ishisone was blocked by a group of Mogami troops led by Satomi Minbu's brothers, Satomi Sabu and Satomi Higashi Ichimasa, and after learning that Yokota was killed, they began to retreat west of Kawaguchi, and when they were pursued by Mogami's army, Naito Saemon was killed, and Shibe Mitsunaga retreated to the Ishi area. Mogami took advantage of the victory and tried to hang the stone. However, the Uesugi defenders fought back, and finally the two armies withdrew their troops due to fatigue.

The Battle of Kamiyama was the worst defeat suffered by the Uesugi army since its attack on Mogami, and it not only lost several generals such as Yokota Yoshitoshi and Naito Saemon, but also failed to realize the strategic concept of capturing Kamiyama Castle and then besieging Hasedo Castle. It has to be said that it is a major blow to Naoe.

Knowing that Kamiyama Castle was defeated and suffered heavy losses, Naoe Kanesui was helpless, and the Uesugi army had besieged the castle for five days without achieving any results, during which Naoe continued to mobilize nearly 25,000 troops to besiege the castle. Including Shida Yoshihide who captured Shiraiwa Castle, Shimoyoshitadashi who captured Tani Castle, Nakajo Mitsumori who captured Toriya Mori Castle, and Shibe Mitsunaga who had just retreated to Nakayama Castle, and specially sent Mizuhara Jinken, who had performed well in the Battle of Sugawa, to the eastern foothills of Tanibashi Fujin Mountain to guard against Mogami Shogami in the direction of Yamagata Castle.

On the third day of the third month of March, fifteen days after the siege of the city, Naoe Kaneji received a secret letter from Honjo. Knowing that Date Masamune was defeated at Matsukawa and was about to retreat to his skills, and that the remaining Masakai was also interested in retreating to Imadeyama Castle, he decided to take the opportunity to launch a general attack on Hasedo Castle. He took the spearhead of Keiji Maeda, Hidekuni Nakatsukawa, Mototsuna Kurakano, Aoyagi Nagatada, and Yasunobu Shinosui, and cooperated with the iron artillery team of Aomigawa Books to launch an offensive against Hasedo Castle.

Inside Hasedo Castle, the iron artillery teams of Fukase Shisuke and Ichikawa Wakasa Mamoru returned fire, and the two sides opened fire on Tsuchihori outside the castle. When the Uesugi army attacked the castle gate, the Mogami army, including the Hasedo group of Shimura Takaharu, the Kokuni group of Okoku Daizen, the Naizawa group of Mamoru Sakaki, the salmon Nobu group of Tsunashi Sasaki, the mountain field side group of Goto Shogun, and the tendo group of Mamoru Kusakari rushed out of the castle.

In the fierce battle, the Uesugi family's generals Okaya Bichu and Baba Jiro Beibei were killed, and the Mogami family also lost dozens of retainers. In the next five days, Naoe Kanesuke organized several more attacks, although they were all repulsed from the top, but due to the lack of reinforcements, the situation in the castle became increasingly difficult, and finally there were less than 3,000 people left, and as a reinforcement, the remaining Masakai strictly guarded the Sugawa line according to Date Masamune's orders, and was unwilling to rush to the aid of Hasedo to participate in the defense of the castle, so the balance of victory was gradually tilting in favor of Naoe Kanesu.

However, Naoe Kanesuke never expected that just when the capture of Hasedo was already in danger, he received an urgent report from Uesugi Keikatsu, saying that Hideho had personally led the crusading army to Aizu on February 28, and ordered him to immediately lead his troops back to Wakamatsu Castle to prepare for the battle.

According to Naoe's assumption, it will take at least a month for Hideho to send troops, and during this time, the Uesugi family will be able to suppress the Mogami family by concentrating their superior forces, and then cede some of the Mogami and the Date family to maintain harmony to ensure that there is no worry behind them, and then return to Aizu to prepare for war. Although Hideho was sent out a month after the start of the war, the Uesugi family did not take advantage of this time, but spent twenty days under Hasedo Castle, and instead of suppressing Mogami Yoshimitsu, they suffered heavy losses and faced Date Masamune's sword soldiers, which was even worse than before the war.

Naoe Kanesuke wanted to take a desperate gamble to capture Hasedo Castle first and then return to Wakamatsu, but Uesugi Keikatsu's continuous urging for the next three days forced him to withdraw from the siege. Late at night on the 10th day of the first month of March, Naoe Kanesu ordered Aoba Irido and Anti-Machi Daizen to repair the Kogoe Street to prepare for the withdrawal, and he divided the whole army into thirteen sections, and ordered Haruto Yen Tadashi and Shinai Yasunobu to go first, and Mizuhara Jinken and Mizoguchi Saoma to help the army. The next day, when it was light, Kanesui ordered the camp to be set on fire, and the whole army began to retreat along the Kogoe street from the Sugasawayama main camp outside Hasedo Castle, but Mogami thought that this was a ploy by Naoe Kanesui and did not dare to leave the city, which bought time for the retreat of the Uesugi army.