Shima Sakon (島 左近; June 9, 1540 - October 21, 1600) was a samurai of the Sengoku period.
Also known as Shima Kiyooki (島 清興), Shima Tomoyuki or Shima Katsutake, he was initially a servant of the Tsutsui clan. Together with Ukon Shigenobu they were known as the right and left hands of Tsutsui Junkei.
After Junkei's death in 1584 he decided to give up the warrior life. He returned to the battlefields when he joined the forces of Ishida Mitsunari, who offered him a generous reward. There was a saying among the people of the time, "Ishida Mitsunari does not deserve two things, Shima Sakon and Sawayama Castle."
During the Battle of Sekigahara Shima served as one of the senior generals of the Western forces. The day before the battle he reported a great success against the eastern forces in the battle of Kuisegawa.
Some sources report that his men were arquebusiers and he also had cannons at his disposal. He quarreled shortly before the battle with Shimazu Yoshihiro when the latter suggested a night attack which Shima opposed.
However he played an important role in the battle, and is identified as one of the glue that held together the different daimyō of the Western forces, not all of whom were happy to follow Mitsunari.
During the battle he commanded only 1,000 samurai, protecting Mitsunari and his headquarters on Mount Sasao, taking part in the fiercest fighting of the day. Shima's son was killed in battle in front of his father, and Shima himself was seriously wounded by the musket fire of a Kuroda Kanbei samurai, Nagamasa, early in the battle.
Nevertheless, he returned again to the battlefield until his servants lost sight of him. At the end of the battle, the eastern troops were immediately ordered to find his head and bring it to Tokugawa Ieyasu. Despite a long search Shima's head was never found. According to some stories, it seems that his second son picked it up on the battlefield and made it disappear.
However, other sources report that he died a month later from his wounds or trying to escape.