Matsudaira Chikayoshi served as a bushō during the Sengoku period. He was the third head of the Takenoya-Matsudaira family. Founded by Matsudaira Moriie, the Takenoya-Matsudaira were an illegitimate branch of the Matsudaira clan based in Takenoya in the Hoi District of Mikawa Province.
In 1485, Chikayoshi was born as the eldest son of Matsudaira Morichika.
From the era of Moriie as the first head of the family until Chikayoshi as the third head of the family, they served several generations of the main branch of the Matsudaira clan including Matsudaira Chikatada and Matsudaira Kiyoyasu, demonstrating their allegiance on the battlefield.
In 1531, Chikayoshi died at the age of forty-seven and was succeeded by his son, Matsudaira Kiyoyoshi.
His grave was built at the Ryūtai Temple in Takenoya.
The graves of Matsudaira Moriie (first head), Matsudaira Moriie (second head), Matsudaira Chikayoshi (third head), and Matsudaira Kiyoyoshi (fourth head) are located to the west of the Shiotsu Middle School in Gamagōri in Aichi Prefecture.