Introduction: ASPIRE Excellence Awards in Student Assessment are offered to medical schools with innovative and comprehensive assessment programmes adjudged by international experts, using evidence-based criteria. The journeys of three ASPIRE-winning medical schools toward “assessment excellence” are presented. These schools include Aga Khan University Medical College (AKU-MC), Pakistan, Southern Illinois University School of Medicine (SIUSOM), USA, and University of Leeds School of Medicine, UK. Methods: The unfolding journeys highlighting achievements, innovations, and essential components of each assessment programme were compared to identify differences and commonalities. Results: Cultural contextual differences included developed-versus-developing country, east-west, type of regulatory bodies, and institutional-versus-national certifying/licensing examinations, which influence curricula and assessments. In all, 12 essential commonalities were found: alignment with institutional vision; sustained assessment leadership; stakeholder engagement; communication between curriculum and assessment; assessment-for-learning and feedback; longitudinal student profiling of outcome achievement; assessment rigor and robustness; 360° feedback from-and-to assessment; continuous enrichment through rigorous quality assurance; societal sensitivity; influencing others; and a “wow factor.” Conclusions: Although the journeys of the three medical schools were undertaken in different cultural contexts, similar core components highlight strong foundations in student assessment. The journeys continue as assessment programmes remain dynamic and measurement science expands. This article may be helpful to other institutions pursuing excellence in assessment.