Originally Tokuhoji Temple belonged to the Tendai school of Buddhism, but changed affiliation to the Jodo Shinshu (True Pure Land) school after a visit from the influential monk Rennyo (1415–1499). Rennyo was the leader of the Jodo Shinshu school at the time and is said to have stopped in Wakasa on the way from Yoshizaki (now in the city of Awara, Fukui Prefecture) to Kyoto in 1475, spending about a hundred days in the area. He stayed at Tokuhoji Temple for some time, and his teaching inspired temple monks to convert to the Jodo Shinshu. A hanging scroll titled Funaji no Myogo (“Buddha’s Name Written at Sea”), still kept as a treasure at Tokuhoji, displays calligraphy supposedly done by Rennyo during the sea voyage from Yoshizaki. The six kanji characters read “Namu Amida Butsu” (“I take refuge in Amida Buddha”), an invocation of Amida’s name chanted as a prayer for rebirth in a Buddhist Pure Land.
In 1570, the powerful warlord Oda Nobunaga (1534–1582) traveled from Kyoto through Kumagawa-juku during a military campaign against Asakura Yoshikage (1533–1573) in Echizen Province. Nobunaga and his commanders, Toyotomi Hideyoshi (1537–1598) and Tokugawa Ieyasu (1543–1616), spent a night in Kumagawa-juku on this journey. A biography of Nobunaga titled Shincho koki states that he stayed at the residence of Matsumiya Genba, one of his retainers, while Ieyasu, the future founder of the Tokugawa shogunate, is said to have lodged at Tokuhoji Temple. After that, a pine tree on the temple grounds was named “Ieyasu’s Resting Pine.” The tree has since withered and died, but the remains of the trunk are exhibited at the nearby Kumagawa-juku Museum (Shukubakan).
Tokugawa Ieyasu was enshrined at the grand Nikko Toshogu Shrine after his death, and Emperor Go-Mizunoo (1596–1680) provided calligraphy of the kanji characters of his posthumous name, Tosho Daigongen, that were carved on the nameplate now hanging on the shrine’s richly decorated Yomeimon Gate. A calligraphic work by Emperor Go-Mizunoo with the same characters, said to have been a draft, has been kept as a treasure at Tokuhoji for centuries.
A memorial stone pagoda in the temple graveyard is dedicated to the Numata family, who were the lords of Kumagawa Castle. Jako (1544–1618), a noblewoman famous for defending Tanabe Castle during a siege in 1600 alongside her husband Hosokawa Fujitaka (also known as Hosokawa Yusai, 1534 –1610), was a daughter of the Numata clan.