Structural reliability and structural robustness, from different research fields, are usually employed for the evaluative analysis of building and civil engineering structures. Structural reliability has been widely used for structural analysis and optimization design, while structural robustness is still in rapid development. Several dimensionless evaluation indexes have been defined for structural robustness so far, such as the structural reliability-based redundancy index. However, these different evaluation indexes are usually based on subjective definitions, and they are also difficult to put into engineering practice. The mathematical relational model between structural reliability and structural robustness has not been established yet. This paper is a quantitative study, focusing on the mathematical relation between structural reliability and structural robustness so as to further develop the theory of structural robustness. A strain energy evaluation index for structural robustness is introduced firstly by considering the energy principle. The mathematical relation model of structural reliability and structural robustness is then derived followed by a further comparative study on sensitivity, structural damage, and random variation factor. A cantilever beam and a truss beam are also presented as two case studies. In this study, a parabolic curve mathematical model between structural reliability and structural robustness is established. A significant variation trend for their sensitivities is also observed. The complex interaction mechanism of the joint effect of structural damage and random variation factor is also reflected. With consideration of the variation trend of the structural reliability index that is affected by different degrees of structural damage (mild impairment, moderate impairment, and severe impairment), a three-stage framework for structural life-cycle maintenance management is also proposed. This study can help us gain a better understanding of structural robustness and structural reliability. Some practical references are also provided for the better decision-making of maintenance and management departments.