The Zeelandbrug serves as an important connection between Noord-Beveland and Schouwen-Duiveland. The bridge completed construction in 1965 using the balanced cantilever method and has been in operation for nearly 60 years. After the passage of these years, the current status of the bridge’s bearing capacity is unknown. Monitoring devices can be applied to obtain more information about the bridge’s condition and to help extend its lifespan. Hence, this study aims to investigate the application of monitoring strategies for the Zeelandbrug. As part of the process of obtaining the monitoring plan, this research also aims to gain a better understanding of the bridge’s structural behaviour. To achieve this, a linear Finite Element Model using one-dimensional beam elements was developed for the Zeelandbrug. This model was used to evaluate how the settlement of a support affects the magnitude of shear forces within the bridge’s superstructure. A structural assessment on the bridge’s superstructure was conducted, with in longitudinal direction incorporating the additional shear forces resulting from a support settlement. Through this assessment, failure modes were identified together with their associated physical parameters. Lastly, a brief investigation was performed on monitoring strategies that can be applied to monitor these parameters.