The hydraulic pressure generating device includes a regulator (spool valve) formed by a cylinder body, a spool which slidably moves within the cylinder body, a pilot chamber in which a pilot pressure which is a hydraulic pressure moving the spool along in an axial direction is inputted and an output chamber out of which an output pressure which is a hydraulic pressure corresponding to the pilot pressure is outputted, wherein the hydraulic pressure generating device further includes a spool position obtaining portion which obtains a relative position of the spool relative to the cylinder body and a pilot pressure controlling portion which controls the pilot pressure based on the relative position obtained by the spool position obtaining portion.