A fluid pressure cylinder includes: a piston rod; a cushioning chamber that decreases in capacity in accordance with extension of the fluid pressure cylinder; a communication passage that allows the cushioning chamber and an in-rod chamber to communicate with each other; a throttle passage that exerts a cushioning function by applying resistance to a flow of a working fluid from the cushioning chamber to the in-rod chamber; a check valve that is provided in a piston, allows the in-rod chamber and a driving chamber to communicate with each other, and has a checking function for permitting only a flow of the working fluid from the in-rod chamber to the driving chamber; and a pilot passage that is formed in the piston and disables the checking function by guiding a pressure in the cushioning chamber to the check valve as a pilot pressure.