The integration of business flow status updates creates a framework for dynamically evaluating operation and maintenance activities, and that assessment is an essential component of achieving intelligent management and control. Highway managers have relied on the operation and maintenance system to integrate business initiatives that improve performance at the organizational and individual levels recently. There are a few studies considering the actual accident or road infrastructure to improve the quality of the highway, but they ignore the power of operation and maintenance (O&M) management involving multiple parties. Furthermore, there is no comprehensive scale to measure the effect of implementing management measures. Therefore, this paper aims to develop a comprehensive multidimensional evaluation framework that considers the integration of the actual business and the objective environment from four aspects: worker, equipment, environment, and management measures. The proposed framework evaluates the current O&M performance with the improved Technique for Order Preference by Similarity to an Ideal Solution (TOPSIS) model, which is used to interpret the comprehensive index results, and highlights the differences and variations of the factors that influence the evaluation results based on the deconstruction analysis. We utilize a mixed dataset of the Hong Kong-Zhuhai-Macao Bridge (HZMB) for two consecutive years to evaluate the performance of each month. The results show that the evaluation framework can effectively measure the O&M performance, and “Worker- Quality of daily inspection work” was identified as the most critical factor affecting the O&M performance. In particular, a comprehensive multiparty operational status assessment helps to review and revise current management strategies for targeted improvements that will enhance the safety and quality of management.