An extensive study of the flexural performance of monoblock prestressed concrete sleepers in a light rail system was conducted as part of a research program funded by the Federal Transit Administration. Five consecutive sleepers deployed on the track were instrumented with strain gauges at their critical design cross-sections (center and rail seats) to obtain relevant flexural information during an uninterrupted period of 14 months. Results were compared with the projected design capacities obtained from the application of current design standards, resulting in glaring differences. The current design methodologies were deemed insufficient for the development of optimal design solutions for light rail applications. Furthermore, structural reliability analysis is employed to study the flexural capacity of the sleeper design. A capacity model based on the material and geometric properties of the sleeper design was developed. The demand model was derived from the field flexural data of over 27,000 train passes, fitting this information to predefined probability distributions. Four limit-state functions were defined to represent the typical flexural failure modes. The probability of failure was calculated using first-order reliability method, second-order reliability method, and Monte Carlo simulation. Ultimately, the analysis yielded consistent results for the three methods, showing largely low probability of failure at both design cross-sections under the studied demand level. In conclusion, the sleeper’s capacity was higher than the existing field demands, indicating an overly conservative design approach.