In the Sengoku period, under Tokugawa Ieyasu (who was the head of what was formerly the main Matsudaira family line), the Sakai became chief retainers.

Tadatsugu, a vassal of Tokugawa Ieyasu, was charged with the defense of Yoshida Castle in Mikawa Province.

In 1578, Sakai Ietsugu (1564–1619) succeeded to his father's role as defender of Yoshida Castle.

The Ie- in the beginning of Ietsugu's name was a special honor bestowed by Tokugawa Ieyasu, who intended to emphasize bonds of loyalty with those who were allowed to share in any part of his name.

[4] The Sakai of Tsuruoka (which later grew to 170,000 koku) in Dewa Province were prominent in the late Edo period as a military power.

Charged with the safety of Edo, they were patrons of the Shinsengumi police force, and were very effective in their duties.

Following the surrender of Edo, the Sakai withdrew and returned north to their domain, where they were active in the northern theater of the Boshin War, as well as becoming signatories to the pact that created the Ōuetsu Reppan Dōmei in 1868.

The head of this clan line was ennobled as a "Viscount" in the Meiji period.

[6] Sakai Tadakatsu (1587–1662) was installed in 1634 through 1868 at Obama Domain (103,500 koku) in Wakasa Province .