The influence of cultural diversity on international business negotiation continues to increase in importance as a result of globalization, liberalization of worldwide markets, and the growth of cross-border mergers and acquisitions. Negotiating styles' options and choices are key factors in determining successful outcomes in cross-cultural negotiations. While much research has been conducted on the influence of cultural dimensions on international negotiation styles, the samples and comparative studies have focused mainly on developed regions of the world - the United States of America, Europe, and Asia. This study focuses on the influence of selected cultural dimensions on the negotiating styles of the United States, and Jamaica - a developing Caribbean territory. Previous research in this area was minimal or non-existent. The study engaged tertiary student respondents in both territories and adopted the GLOBE Leadership Scale instrument to measure the effect of six cultural dimensions on cultural practices and cultural values in both countries. Simultaneously, the Glaser and Glaser Negotiating Style instrument was used to measure five different style choices grounded in the Dual Concerns Theory. The findings suggest that US negotiators would demonstrate a higher concern for self than Jamaican negotiators while Jamaican negotiators would show a higher concern for others in the negotiating process. This was also supported by the finding that the higher collectivism culture of the Jamaicans has a significant positive influence on their compromising style approach. Another significant finding was on the gender egalitarian cultural construct which suggests that both the US and Jamaican negotiators would embrace the participation of a greater number of female negotiators in the future. The US would also be more accommodative in their negotiating style where greater gender equity prevails. Power distance as a cultural dimension was not significant on negotiating styles in both countries but it was encouraging to note that power distance gaps would be narrower in the future.