The invention discloses an orientating monitoring device and method for drilling stress. The device is composed of a pressure data collecting instrument, a wire, a pressure sensor, a direction controldevice and a protective shell. The direction control device is composed of a bearing and a counter weight; the protective shell is composed of a cut PVC tube and a steel wire net. Through the counterweight, the testing direction of the stress is determined; through the direction control device, the pressure sensor is kept unchanged in direction when pushed into a drilled hole, and then the direction and intensity of the stress of the drilled hole in a coal roadway are measured accurately. The structure and the method are simple, on-site operation is easy, the dynamic change of the intensityof the stress of the drilled hole can be monitored in real time, and the stress of the drilled hole is tested and evaluated in real time.