More than 30 years after its first implementation, IT outsourcing (ITO) is unanimously considered a critical component of corporate strategy for private and public institutions alike. While implementations of ITO around the world share some common characteristics like typical reasons for outsourcing, key success factors, or dimensions along which they can be classified, extant research also points to regional differences. However, research on this topic, specifically regarding pivotal contract features like contract value, contract length, or pricing methods, is still in its infancy, and quantitative analyses on the subject are particularly scarce. We address this research gap by analyzing data on 14,917 ITO contracts closed between 2007 and 2017 through the lens of cultural regions and three statistical methods. The contribution of our paper is threefold. First, our descriptive analysis points to globally decreasing contract lengths and contract values, confirming previous studies and practice reports. Second, an ANOVA with independent post-hoc testing provides quantitative support for the degree of dissimilarity among individual regions in pivotal ITO contract features. Finally, our quantitative replication of a previous study identifies culture-induced regional differences between USA and Japan regarding the effect of influence factors on ITO contract features.