The Ashikaga clan (足利氏, Ashikaga-shi^?) was a prominent Japanese samurai clan which established the Muromachi shogunate and ruled Japan from roughly 1336 to 1573.

The Ashikaga were descended from a branch of the Minamoto clan, deriving originally from the town of Ashikaga in Shimotsuke province (modern-day Tochigi prefecture).

For about a century the clan was divided in two rival branches, the Kantō Ashikaga, who ruled from Kamakura, and the Kyōto Ashikaga, rulers of Japan. The rivalry ended with the defeat of the first in 1439. The clan had many notable branch clans, including the Hosokawa, Imagawa, Hatakeyama (after 1205), Kira, Shiba, and Hachisuka clans. After the head family of the Minamoto clan died out during the early Kamakura period, the Ashikaga came to style themselves as the head of the Minamoto, coopting the prestige which came with that name.

Another Ashikaga clan, not related by blood, and derived instead from the Fujiwara clan, also existed.

Ashikaga Yoshiteru (足利 義輝^?, March 31, 1536 – June 17, 1565), also known as Yoshifushi or Yoshifuji, was the 13th shogun of the Ashikaga shogunate who reigned from 1546 to 1565 during the late Muromachi period of Japan. He was the eldest son of the 12th shogun, Ashikaga Yoshiharu; and his mother was a daughter of Konoe Taneie (later called 慶寿院 Keijuin). When he became shogun in 1546 at age 11, Yoshiteru's name was Yoshifushi (sometimes translated as Yoshifuji); but some years later in 1554, he changed his name to the one by which he is conventionally known today. His younger brother Ashikaga Yoshiaki would become the fifteenth shogun.

After his father, Yoshiharu, was forced to retire in 1546 over a political struggle with Hosokawa Harumoto, Yoshiteru became Seii Taishogun, albeit a puppet shogun like his father. Yoshiteru was only 11 at the time and his investiture ceremony was held at Sakamoto, Ōmi Province, outside Kyoto.

Yoshiteru had barely been confirmed as shogun when his father Yoshiharu made a truce with Harumoto in order to return to Kyoto. Yet, Harumoto's retainer Miyoshi Nagayoshi parted with Harumoto to take the side of Hosokawa Ujitsuna and the two Hosokawa started a war that drove out Yoshiteru, his father Yoshiharu, and Harumoto as well, from Kyoto. In 1550, Yoshiharu died in Ōmi, unable to return to Kyoto.

Date Masamune (伊達 政宗^?, September 5, 1567 – June 27, 1636) was a regional strongman of Japan's Azuchi-Momoyama period through early Edo period. Heir to a long line of powerful daimyo in the Tōhoku region, he went on to found the modern-day city of Sendai. An outstanding tactician, he was made all the more iconic for his missing eye, and Date was often called dokuganryū (独眼竜), or the "one-eyed dragon".

As a legendary warrior and leader, Masamune is a character in a number of Japanese period dramas. He was played by Ken Watanabe in the popular 1987 NHK series Dokuganryu Masamune.

Date Masamune was the eldest son of Date Terumune, born in Yonezawa Castle (in modern Yamagata Prefecture). At the age of 14 in 1581 Masamune led his first campaign, helping his father fight the Sōma family. In 1584, at the age of 17, Masamune succeeded his father, Terumune, who chose to retire from his position as daimyo. The Date family was founded in the early Kamakura period by Isa Tomomune, who originally came from the Isa district of Hitachi Province (now Ibaraki Prefecture). The family took its name from the Date district (now Fukushima Prefecture) of Mutsu Province, which had been awarded to Isa Tomomune by Minamoto no Yoritomo, the first Kamakura shogun, for his assistance in the Genpei War (1180–85) and in Minamoto no Yoritomo’s struggle for power with his brother, Minamoto no Yoshitsune. Masamune's army was recognized by its black armor and golden headgear.

Ashikaga Yoshimitsu (足利 義満^?, September 25, 1358 – May 31, 1408) was the 3rd shogun of the Ashikaga shogunate who ruled from 1368 to 1394 during the Muromachi period of Japan. Yoshimitsu was the son of the second shogun Ashikaga Yoshiakira.

"The principal beneficiary of these achievements [the solid political and economic standing of the Muromachi Bakufu] was the adult Yoshimitsu, who assumed power in his own right upon the forced resignation of Hosokawa Yoriyuki in 1379" - The Ōnin War - H. Paul Varley: Page 58

"The adult Yoshimitsu dominated Bakufu politics for nearly 30 years, from 1379 until his death in 1408." - The Ōnin War - H. Paul Varley: Page 61

In the year after the death of his father Yoshiakira in 1367, Yoshimitsu became Seii Taishogun at age 11.

Significant events shape the period during which Yoshimitsu was shogun:

Yoshimitsu constructed his residence in the Muromachi section in the capital of Kyoto in 1378. As a result, in Japanese, the Ashikaga shogunate and the corresponding time period are often referred to as the Muromachi shogunate and Muromachi period.