Greenhouse gas (GHG) emissions from the global shipping sector have been increasing due to global economic growth. The International Maritime Organization (IMO) has set a goal of halving GHG emissions from the global shipping sector by 2050 as compared with 2008 levels, and has responded by introducing several international regulations to reduce the GHG emissions of maritime transportation. The impact of GHG emissions’ regulation and measures to curb them have been evaluated in the IMO’s GHG studies. However, the long-term influence of these GHG emission measures has not yet been assessed. Additionally, the impact of various GHG reduction measures on the shipping and shipbuilding markets has not been considered; accordingly, there is room for improvement in the estimation of GHG emissions. Therefore, in this study, a model to consider GHG emission scenarios for the maritime transportation sector was developed using system dynamics and was integrated into a shipping and shipbuilding market model. The developed model was validated based on actual results and estimation results taken from a previous study. Subsequently, simulations were conducted, allowing us to evaluate the impact and effectiveness of GHG emission-curbing measures using the proposed model. Concretely, we conducted an evaluation of the effects of current and future measures, especially ship speed reduction, transition to liquid natural gas (LNG) fuel, promotion of energy efficiency design index (EEDI) regulation, and introduction of zero-emission ships, for GHG emission reduction. Additionally, we conducted an evaluation of the combination of current and future measures. The results showed that it is difficult to achieve the IMO goals for 2050 by combining only current measures and that the introduction of zero-emission ships is necessary to achieve the goals. Moreover, the limits of ship speed reduction were discussed quantitatively in relation to the maritime market aspect, and it was found that the feasible limit of ship speed reduction from a maritime market perspective was approximately 50%.