The invention relates to a penetrating-stretching type pore water pressure measurement device and a measurement method thereof. A projecting segment of a taper penetration head is inserted into a filter pipe and is connected with the filter pipe through a screw thread or a pin. The filter pipe is externally provided with a sleeve pipe and is in sliding fit with the sleeve pipe. The sleeve pipe is tightly pressed on a shoulder of the sleeve pipe and the taper penetration head through a gasket. A bottom of a conduit is arranged on an upper end of the sleeve pipe through screw thread or nestification. According to the device and the method, problems that pore water pressure monitoring and measurement are complex and data is not direct in a saturated soft soil distribution region are solved, the device and the method are especially suitable for the pore water pressure monitoring and measurement of a fine grain soil layer with formation reasons of a fourth system river delta phase, an oxbow lake phase, a lake phase, a lagoon phase, a marsh phase and the like, measurement of a groundwater table, a perched water level and a confined water head of underground water, underground water monitoring, and water quality layered monitoring and sampling of an underground water environment. Compared with the prior art, the device has the advantages of simple structure, low cost, practicality and convenience, and the measurement method has the advantages of convenience, easy enforcement, convenient operation and reliable data.