We constructed the photometric observation system with a small semi-automatic telescope for the systematic observations of eclipse timings of eclipsing binary stars. The system is consisted of a Paramount GT-1100s mount system, a Celestron 14 optical system, and a SBIG ST-8 camera. We developed the OBSTOOL S/W which controls the telescope and the CCD camera using the COM(Component Object Model) supported by the softwares, The Sky and MaximDL. The system performs photometric observations of a variable, comparison and check stars by moving the telescope to the chosen star separately in a similar way such as the method of photoelectric observation. We wrote perl scripts which enable a data handling pipeline for the obtained data to be classified by each of date, object and filter. And thus the images are easily preprocessed using the IRAF S/W package. Eclipse light curves of some eclipsing binary stars observed with this system are presented.