Expeditionary Airfield (EAF) surfacing systems are designed to create temporary aircraft operating surfaces. Modeling the service life of EAF surfacing systems including the matting system, aircraft, and subgrade, has historically proven difficult, exacerbated by variability between systems and the multitude of mechanisms that can constitute failure. The study presented herein outlines the development and implementation of a performance modeling approach that includes a multi-scale scheme that accounts for local characteristics of the connection points of the EAF matting system, coupled to the global characteristics of the matting array to predict cyclic passes to failure. Finite element studies were conducted for an EAF surfacing system brickwork configuration subjected to aircraft strut loads over varying California Bearing Ratio (CBR) subgrades to calibrate a transfer function to full-scale trafficking experiments. The proposed framework is then used to predict the rate of subgrade deformation for additional lay patterns, which successfully ranked the performance of each relative to full-scale trafficking experiments. An approach is proposed to couple the rate of subgrade deformation with local finite element models to capture increasing joint damage as permanent deformation accumulates, and supplemented by a variable amplitude cycle counting and damage accumulation algorithm that yields reasonable agreement with full-scale experiments while capturing the transition in failure mechanisms at higher CBR values. The results of the study presented herein captures the propensity for end connector and subgrade failure over a range of subgrade CBRs and shows promise for a broader performance framework that can be extended to other EAF surfacing systems, aircraft types, and specific matting lay patterns.