Numerous studies have shown that the oppressiveness brought on by high-rise buildings can be somewhat mitigated by landscapes. However, there is a lack of research that specifically examines the relationship between courtyard landscape layouts and spatial oppressiveness. This study focuses on the relationship between the landscape layout of a small courtyard and spatial oppressiveness. It entails tests that are conducted in two phases of experiments that examine visual, behavioral, and psychological aspects. In the first experiment, participants were asked to freely explore four sample scenarios without any predetermined outcome, and their behavioral coordinates were recorded as behavioral data. Using the semantic differential (SD) method, participants in the second experiment used four example panoramic landscapes to assess oppressiveness and supply psychological indicators (including oppressiveness, attractiveness, territoriality, and desire to stay). Additionally, this study quantified the visual elements’ solid angles in the scenes through panoramic image segmentation. The results ultimately show that landscape layouts, particularly the surrounding and dispersed layouts, are more effective in alleviating the oppressiveness induced by surrounding buildings compared to the centralized layout. Furthermore, the study explains the process of how landscape layouts mitigate oppressiveness through visual elements and behavioral intention.