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Abstract: Implementing a truck appointment system at container terminals is a successful method to smoothen peaks in truck arrivals and thereby reduce truck waiting times and congestion in the port area. In spite of extensive literature on its impact on container terminal productivity, other stakeholders in the port drayage network have been studied only occasionally. This paper aims to analyze different strategies of time window selection for port drayage companies considering different company sizes and competitor’ strategies. The analysis is done by means of a discrete event simulation model. The results show that an early booking of appointments at container terminals is beneficial for the success rate of trucking companies. Furthermore, it is highlighted that the truck turn time of small-sized companies in this network is higher than the one of large-sized companies