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Born in 1519 as the third son of Imagawa Ujichika, the 10th Imagawa head in Suruga. Becoming 11th head through his elder brothers' deaths, he stabilized the clan with the counsel of his brilliant advisor Taigen Sessai, suppressing internal uprisings including the Hanakura Revolt. He updated the Imagawa house law code, establishing strong internal order and administration. Militarily, he secured his flanks with the Tripartite Alliance with Takeda Shingen and Hojo Ujiyasu, then dominated Suruga, Totomi, and Mikawa—three provinces along the Tokaido—earning the title "Greatest Archer of the Eastern Seaboard." He wielded strong influence over Mikawa through his backing of Matsudaira Hirotada, keeping the young Tokugawa Ieyasu as a hostage. In the fifth month of 1560, he marched west with some 25,000 troops toward Kyoto. Entering Owari, he was caught in a surprise attack by Oda Nobunaga's small force during a downpour at Okehazama and was killed at age 42. This miraculous Nobunaga victory became the starting point of his rise to national power. Long caricatured, Yoshimoto is increasingly recognized as an outstanding administrator.

Often caricatured as an effeminate courtier, but in reality a capable ruler and general. His domain flourished in what was called "the Great Peace of Tokai."

Long stigmatized as careless for his death at Okehazama, he is being reassessed as an excellent domain manager. Historically significant as the catalyst for Nobunaga's rise.