This study evaluates the structural behavior of connected long-span beams applied for excavation in urban areas with a narrow street. Generally, the reliability of the connection is reduced owing to the defect of the upper flange in the connection. An improved connection part was developed to complement the defects in the connected long-span beam. A finite element analysis based on a commercial program, ABAQUS, was employed to evaluate the behavior of the improved connection part. A numerical analysis model was proposed to analyze the high-strength bolt connection and the composite behavior of steel and concrete applied to the improved connection. The suitability of the proposed numerical analysis was verified by comparing the experimental and numerical analysis results of the references. Using the proposed numerical analysis method, the improved and general connections were analyzed and compared with each other. The stress distribution and elastic-plastic behavior of the long-span beam were analyzed numerically. The analysis confirmed that 25% of the compressive stress was improved, resulting in the improvement of structural safety and performance.