The rise in the ship size and diversity causes the technological and structural change of harbor cranes. This change requires equipment selection to be made in line with port capacity plans, efficiency targets, current requirements and objectives. Therefore, the main aim of the study is to compare the operational efficiency of port container handling equipment from ships to shore in practice and, finally, to select the right equipment. In this study, the “Small-N” comparative analysis method was preferred in order to determine the strengths and weaknesses of the equipments. The data belonging to 2 MHC (Mobile Harbor Crane) and 1 SSG (Ship to Shore Gantry Crane) equipments were used by means of a unique simulation software developed for this study. The study findings show that the selection of port equipment varies according to the hourly movements of the equipment. As a consequence of the ship owners that only focus on the service provided by the port, port-line agreements are made up to the minimum number of movements. At this point, the number of cranes and movements is limited due to the lateral movements of MHCs and as a result, STSs provide a significant competitive advantage in container operations.