This study examines the evolution of contemporary Latvian architecture by analysing the Latvian Architecture Award Grand Prix-winning works from 1995 to 2024. Using the Davos Baukultur Quality System (DBQS) as an analytical framework, the research integrates discourse analysis of jury statements and architects’ narratives with image analysis of architectural drawings and photographs. The study identifies 44 design issues across eight criteria – governance, functionality, environment, economy, diversity, context, sense of place, and beauty – demonstrating the shift in architectural priorities over time. Notably, functionality and aesthetics dominated early discussions, while later projects increasingly emphasized sustainability, cultural identity, and social inclusion. The introduction of the DBQS in 2021 marked a significant period, with projects showing heightened attention to community engagement and environmental challenges. This analysis highlights Latvian architecture’s dynamic engagement with cultural, social, and environmental concerns, offering significant insights into contemporary architecture’s evolving professional and societal role through the lens of the Latvian Architecture Award.