Derinkuyu Underground City, located in the Cappadocia Region of Turkey, is an important structure not only for its antique and archaeological characteristics, but also as a structure in terms of the long-term stability of underground rock structures excavated by mankind. The authors carried out some observational, experimental and theoretical rock mechanics studies in the region from 1996 in the context of a research project supported by the Ministry of Education, Culture, Sports, Science and Technology of Japan for the assessment of the long-term behaviour of Derinkuyu Underground City, and these studies are still continuing. In addition to the monitoring of the environmental conditions such as temperature, moisture and air pressure, they also installed acoustic emission (AE) and electrical potential (EP) measurement systems to monitor the behaviour and response of the surrounding rock at the fifth and seventh floors of the underground city. In this article, the geology, seismicity and state of stress of the Cappadocia Region, climatic conditions in the underground city and its vicinity, short- and long-term behaviours of the surrounding rock, its index and mechanical properties, and effects of water content and freezing-thawing processes were investigated. The stability of Derinkuyu Underground City was also evaluated using theoretical and numerical methods, and the results were presented. Furthermore, its implications in modern geoengineering are also discussed.