In recent decades, wood structures have gained significant attention for their ecological benefits and architectural versatility. The performance of wood, a popular construction material, often depends on the integrity of its connections. This study focuses on bolted glulam timber connections, which are strong but prone to cracks that pose structural health challenges. Traditional crack evaluation methods are manual, time-consuming, and error-prone. To address these issues, this research proposes a two-stage performance evaluation method. In the first stage, an innovative approach called ‘Enhanced Deep Line Segment Detection’ (Deep LSD), a non-supervised machine learning technique, is used for crack detection without relying on large, annotated datasets, thus enhancing efficiency and adaptability. In the second stage, cyclic loading assays simulate varying damage stages to collect data and establish a correlation between crack states and connection damage. The Park and Ang damage model is employed within this framework to assess the extent of damage. The efficacy of enhanced deep LSD is confirmed by comparing detected crack areas with ground truth measurements, yielding a high R-squared value of 0.98 and a minimal error margin of 1.41. Additionally, a damage index based on the Chinese standard (GB/T 24335-2009) is used to classify damage across different connection groups, ensuring robustness and alignment with established practices.