Analyzing dynamic performance between pantograph and contact wire depends on mechanical and electrical conditions such as contact force, currents, aerodynamics of pantograph and tension of overhead contact wire. For the characteristic of dynamic performance between pantograph and overhead contact wire, various evaluation systems are used to measuring of the interaction of the contact line and the pantograph. Among the various methods, the contact force and percentage of arcing are intended to prove the safety and the quality of the current collection system on the train. However, these methods are only capable of measuring on the train which are installed measurement systems. Therefore in this paper, a track-side monitoring system was implemented to measure electrical characteristics from active overhead contact wire systems in order to constantly estimate current collection performance of railway operation. In addition, a method to analyze loss of contact phenomena was proposed. According to simulation results, the proposed system was capable of measuring abnormal electrical behavior of pantograph and contact wires on the track-side. The advantage of the proposed system is possible to detect loss of contact or any other electrical abnormalities of all types of trains within sections from sub to sub without the need to install any on-board equipment on trains.