He learned his swordplay in the following way throughout his life: He learned it from Kyuga OKUDAIRA (Kyugasai was one of his names as a swordsman), a founder of swordplay as well as his retainer, for seven years from the Battle of Anegawa, employed Tadaaki ONO (recommended by Ittosai ITO in the Itto-ryu school of swordplay) as the swordplay instructor for Hidetada at a stipend of a 200 koku of rice a year in 1593, and also employed Munenori YAGYU in 1594 (Ieyasu fought with Muneyoshi YAGYU in a swordplay match and was defeated with Munenori using no sword, and therefore, ordered Muneyoshi to serve the bakufu as a swordplay instructor, but he declined the order because of his advanced age).
剣術開祖で家来でもある奥平久賀（号の一に急賀斎）に姉川の戦いから7年間師事、文禄2年（1593年）に小野忠明を200石（一刀流剣術の伊東一刀斎の推薦）で秀忠の指南として、文禄3年（1594年）に新陰流の柳生宗矩（柳生宗厳と立ち会って無刀取りされたため宗厳に剣術指南役として出仕を命ずるも、宗厳は老齢を理由に辞退）を召抱える、など、生涯かけて学んでいた。