Hosokawa Shigeyuki served as a bushō and shugo daimyō during the late-Muromachi and Sengoku periods. Shigeyuki was a member of the shōbanshū for Ashikaga Yoshihisa (the ninth shōgun of the Muromachi bakufu).  The shōbanshū comprised the personal retinue of the shōgun to arrange banquets and host visitors to the shōgun’s palace.  He was the fifth head of the Hosokawa-Awa military family and the military governor of Awa, Mikawa, and Sanuki provinces.  Shigeyuki was the grandfather of Hosokawa Sumimoto who inherited the Hosokawa-Keichō family – the main branch of the Hosokawa clan.

Shigeyuki was born as the son of Hosokawa Norisuke.  He was later adopted as a designated successor of his uncle, Hosokawa Mochitsune.

In 1449, he inherited the headship of the Hosokawa-Awa military family and became the military governor of Awa and Mikawa provinces.  At the time of his coming-of-age ceremony, he received one of the characters from the name of Ashikaga Yoshishige, the eighth shōgun of the Muromachi bakufu (later known as Ashikaga Yoshimasa) and adopted the name of Shigeyuki.

In 1454, after Ashikaga Yoshimasa ordered multiple daimyō to eliminate Yamana Sōzen, Shigeyuki was chosen to serve as the commanding general, but just before the deployment, the plans were canceled upon an urgent appeal by Hosokawa Katsumoto, the deputy shōgun, to Yoshimasa.  In 1462, upon orders of the bakufu, Shigeyuki was commanded to kill Hatakeyama Yoshinari so he traveled from Kyōto to Kawachi Province and participated in a prolonged siege of Dakeyama Castle.  This event is known as the Siege of Dakeyama Castle.

In Mikawa, conflict continued with the prior military governors, the Isshiki clan.  In 1465, kokujin, or provincial landowners, including Maruyama Nakatsukasa Nyūdō and Ōba Jirōzaemon, launched an uprising in the Nukata District.  Matsudaira Nobumitsu and Toda Munemitsu, under the command of Ise Sadachika, the director of the mandokoro (the organ of the bakufu responsible for adjudicating financial and territorial disputes) appeared to be orchestrating the incident from behind the scenes but Shigeyuki did not have rights to direct them so, via Sadachika, he appealed to the shōgun family and, upon orders of the bakufu, had them suppress the uprising.

During the Ōnin-Bunmei War, Shigeyuki affiliated with the Eastern Army led by Hosokawa Katsumoto.  In 1467, Shigeyuki fought against the Western Army in the streets of Kyōto.  These events are known as the Battle of Kamigyō and the Battle of Shōkoku Temple.  In 1473, he was appointed as the military governor of Sanuki Province.  In 1476, Tōjō Kuniuji, the deputy military governor of Mikawa, was attacked by Isshiki Yoshinao of the Western Army and took his own life while Shigeyuki suspended his service to the bakufu.  In 1478, Yoshinao abandoned Mikawa so he engaged in service to the bakufu again.  Thereafter, however, the Hosokawa clan was not appointed as the military governor of Mikawa.  Provincial landowners, led by the Saigō clan, descendants of the deputy military governors serving the Nikki clan (the original military governors of Mikawa), competed among one another for influence in Mikawa.  While grieving at the loss of his daughter on 9/16 of Bunmei 10 (1478), Shigeyuki entered the priesthood and transferred headship of the clan to his lineal heir, Hosokawa Masayuki.

After entering the priesthood, on 1/15 of Bunmei 11 (1479), Shigeyuki departed for a tour of several provinces.  He worshiped at the Kumano-Sanzan shrines, but his sudden entry into the priesthood and accompanying retirement shook the clan, giving rise to a faction of retainers seeking to oust his son, Masayuki.  This caused Shigeyuki to quickly return.  Thereafter, tensions between Masayuki and the retainers persisted.  After Miyoshi Yukinaga, a senior retainer of Shigeyuki, incited the Tokusei ikki, rather than punish him, Masayuki gave him more responsibilities.  This stirred resentment among senior retainers in the capital such as the Tōjō and Inoo clans.  On 7/16 of Bunmei 17 (1485), these clans betrayed Shigeyuki and Masayuki, returned to Awa Province, and, in the tenth month, launched a rebellion.  As a result, Shigeyuki and Masayuki hurriedly departed the capital and went to Awa to suppress the rebellion.

In 1488, Masayuki died early in Kyōto so his second son, Hosokawa Yoshiharu, succeeded him.  At the time, Shigeyuki was in Awa to manage the aftermath of a rebellion so he could not attend the funeral for Masayuki held at the Nishiyama-Hōkō Temple.  In 1497, Yoshiharu also died while his grandson, Hosokawa Yukimochi, was still young so Shigeyuki served as his guardian.  Under another theory, after the death of Yoshiharu, Shigeyuki resumed responsibilities as the military governor of Awa and remained in this position until his demise.  Alternatively, even if he ostensibly transferred the role of military governor to Yukimochi, he may have retained the real authority until his death.

In 1504, Yakushiji Motokazu, a senior retainer of Hosokawa Masamoto, the deputy shōgun, revolted in a bid to oust Masamoto, but was killed instead.  Suspicious that Shigeyuki was behind the incident, Masamoto plotted to eliminate him.  Meanwhile, Miyoshi Yukinaga aimed for a preemptive strike by attacking Masamoto’s base in Awaji.  Masamoto dispatched an army to Sanuki and Awa to subdue them while Masamoto himself led forces to Awaji.  Later, Hosokawa Sumimoto (another one of Shigeyuki’s grandsons) was tendered for adoption by Masamoto and the warring parties settled.  In 1506, Sumimoto and Yukinaga, as his deputy, arrived in the capital.  In 1507, another one of Masamoto’s adopted sons, Hosokawa Sumiyuki, orchestrated the assassination of Masamoto in an event known as the Lord Hosokawa Incident.  This triggered a prolonged succession struggle between Sumimoto and another adopted son, Hosokawa Takakuni, known as the Conflict between the Hosokawa.  After serving as a Zen monk at the Rokujō Temple which he revived, Shigeyuki absconded to support his grandson, Sumimoto.  In 1511, after suffering a defeat by Takakuni at the Battle of Funaokayama, Sumimoto returned to Awa and Shigeyuki died that same year.  He was seventy-eight years old.

His grave is located at the Jōroku Temple in the town of Jōroku in the city of Tokushima in Tokushima Prefecture.  A portrait of Shigeyuki is kept at this temple.

Character

Shigeyuki is known as a refined individual representative of the Higashiyama culture.  He had exchanges with renga poets including Gyōe, a monk from the Tendai sect and Inawashiro Kensai, and Ōsen Keisan.  He provided backing for a compilation of poems and was presented transcripts from Kensai.  Shigeyuki was also conversant in the arts of painting, inu-ōmono (archery competition with dogs), kemari (kickball), and sarugaku (traditional dramatic arts).

After the Hosokawa family of the deputy shōgun, Shigeyuki was trusted and respected by the bakufu and the Ashikaga shōgun family.