May 13, 1397 (Ōei 4, 16th day of the 4th month): Construction begun on Kinkaku-ji.
1397 (Ōei 4, 8th month): an Imperial ambassador is dispatched from Emperor Go-Komatsu to the court of the Hongwu Emperor of China.
September 1398 (Ōei 5, 8th month): In the early autumn in the 6th year of the reign of King Taejong of Joseon, a diplomatic mission was sent to Japan.Pak Tong-chi and his retinue arrived in Kyoto. Shōgun Yoshimochi presented the envoy with a formal diplomatic letter; and presents were given for the envoy to convey to the Joseon court.
November 18, 1399 (Ōei 6, 28th day of the 10th month): Ōei Rebellion [ja] (応永の乱, Ōei no ran) begins. Ōuchi Yoshihiro raises an army against shōgunAshikaga Yoshimitsu; and the Ashikaga forces prevail against this opposition.
1401 (Ōei 8, 2nd month): The Imperial Palace was burned.
1401 (Ōei 8): Yoshimitsu sends a diplomatic mission to the court of the Jianwen Emperor of China as a tentative first step in re-initiating trade between Japan and Ming China. The letter conveyed to the Emperor of China was accompanied by a gift of 1000 ounces of gold and diverse objects.
1402 (Ōei 9): A letter from the Jianwen Emperor of China was received by Yoshimitsu; and this formal communication mistakenly accords the title "king of Japan" to the Japanese shōgun.
1411 (Ōei 18): Yoshimochi breaks off relations with China.
1412 (Ōei 19): Emperor Shōkō was made the new sovereign upon the abdication of his father, Emperor Go-Komatsu. His actual coronation date was two years later. Shōkō was only 12 years old when he began living in the daïri; but Go-Komatsu, as a Cloistered Emperor still retained direction of the court and the shōgun was charged with the general superintendence of affairs until his death at age 57 in 1433.
July 18, 1419 (Ōei 26, 26th day of the 6th month): Ōei Invasion (応永の外寇, Ōei no gaikō) was a Joseon military action in Tsushima Province (Tsushima Island). The Joseon military forces were focused on the pirates (wakō) which had established bases from which to raid the coastline of the Korean peninsula. More than 200 ships and 17,000 fighting men took part in this military expedition.
1420 (Ōei 27): Serious famine with great loss of life.
1422 (Ōei 29): Resuragence of southern supporters.
1423 (Ōei 30, 2nd month): Shōgun Yoshimochi retires in favor of his son, Ashikaga Yoshikatsu, who is 17 years old.