This investigation evaluates the performance of Portuguese exports by focusing on the 11 main partners for 1990–2021, considering panel data. Country risk analysis has been frequently used to assess the determinants of international trade in recent years. Empirical studies demonstrate that country risk can affect bilateral relationships between economies, especially in economies with greater geopolitical risk. Next, we refer to the methodology used in this research. In this context, we assessed the stationarity of the variables used in this study. Subsequently, models were used to eliminate bias and endogeneity between the variables. The panel quantile regression model allows us to understand the behaviour of variables across different quartiles. The empirical study shows that countries with low country risk promote the performance of Portuguese exports. On the other hand, the size of the economies, both the exporting country (Portugal) and the importing countries (commercial partners), is decisive for increasing Portuguese exports. This finding can be explained as a monopolistic competition with the economy’s scale and industrial concentration serving as theoretical support. As noted with previous studies on the gravity model, the common language of Portuguese-speaking countries reduces communication costs and increases Portuguese exports. Furthermore, the econometric model also validates the issue of geographical distance, where this variable has a negative impact on exports, demonstrating that geographical proximity reduces transport costs.