Chitose Sensei started his Tode (karate) training when he was seven years old (1905). His first teacher was a sixty year old man by the name of Unchu (Nigaki) Kamade Arakaki (1840-1920). Arakaki Sensei taught the young Chitose his first kata - Seisan (though there is some dispute about this and it is probably the kata Sanchin that he was taught first). The method of teaching karate in those days was to teach kata. The practice of basics and kumite, which is common today, was unknown. For years the young Chitose practiced the one kata he was taught at age 7. Only after he reached the age of fourteen did Arakaki Sensei teach him his second kata.
When young Tsuyoshi Chitose entered high school he had the opportunity of further training with Sensei Anko Itosu (1832-1916). Itosu was born in Yamagawa Village, Shuri, and was a student of Sokon Matsumura. It is believed Itosu Sensei developed the Chinese corkscrew punch into its present form, and also originated the Pinan (Heian) kata. In April, 1901, Itosu Sensei introduced karate training to the Shuri Jinjo Elementary School as part of the physical fitness training. During 1905 he introduced karate training into the Prefectural Teachers Training College. 
Three years later, under his guidance, karate training was introduced into all Okinawan schools.
One of Chitose Sensei's young school friends was Shoshin Nagamine, who would one day found the Matsubayashi Shorin-ryu style of karate, and become president of the Okinawan Karate Federation. One of their school teachers, later recognized as the greatest karate master of the twentieth century, was Gichin Funakoshi (1868-1957), the father of modern karate and founder of Shotokan (the picture to the left shows Dr. Chitose and Gichen Funakoshi in the middle). Another of Chitose Sensei's classmates was Funakoshi Sensei's son, Gikko (Yoshitaka) Funakoshi.