Moving Target Defense (MTD) concept has been a feasible idea for reducing the possibility of attack happening through alternation attack surfaces or diversification the attribute or parameters of a protected system. As a result of applying MTD techniques to the system, an attacker would have more difficulties in exploiting a vulnerabilities of the target system. This study proposes an evaluation method of MTD systems combined with several different MTD techniques. The proposed method is a primary step in designing an evaluation model for the effectiveness of MTD. The main goal is to estimate the attack success ratio on the MTD systems mitigating from threats of executable binary file or malware injection. With the proposed evaluation method, we expect to prove that the MTD technology can enhance the security of a web server, and can be applied in a real-world information system. As our preliminary work done, we set up a prototype framework to validate the proposed work in a pseudo-experimental environment.