Seaports are crucial interfaces in global intermodal freight transportation networks. Their complex operations, connectedness to external stakeholders, and increasing volumes of goods to be handled make them vulnerable to internal and external disruptions. Research has shown that disruptions in seaports can cause undesirable ripple effects, which negatively impact the operations of the entire transportation network as well as the surrounding economical and societal well-being. Containerized transportation plays a major role in the global trade network. Resilience of seaport container terminals is therefore imperative for a resilient and robust intermodal transportation network. Communication, information sharing, alignment of plans, and shared awareness of unfolding disruptions among planners and decision makers within terminal operations have been identified as important elements to improve the resilience of container terminals. However, in practice, the inter-dependencies between various planning and operational activities, and alignment of solution strategies have been largely overlooked. Addressing this gap, a novel approach for creating awareness of potential strategies for disruption management by training competencies for resilient container terminal operations has been introduced in the form of a simulation game. Several test sessions of a multi-player tabletop game support the following two findings—first, the simulation game can be a useful means to train competencies for resilient transport operations from the perspective of the future planners and decision makers, as well as for soon-to-be professionals in container terminals. Second, the game may help participants to make choices that lead to resilient transport operations in container terminals.