Land is a natural resource, and settlement development is central for human activities. The growth of settlements comes at the expense of natural and agricultural land. Understanding urban growth dynamics, defined in this study as new urban development, can lead to an increased awareness of the stresses on land resources and the suitability of current land use policies. It can also reflect how changes in the economic cycles and planning policies can influence these dynamics. This is even more critical in small island states, where land is a scarce resource. This study uses data extracted from development-planning applications between 1993 and 2019 in order to understand urban growth in the island-state of Malta. A methodology was developed to (i) use web-scraping techniques to extract development-planning applications data from a public online database in order to define development descriptors, (ii) establish keywords that imply growth within the urban area, and (iii) analyse growth in view of local planning zones and regulations. The results show that over the years, there has been a decrease in the share of granted development-planning applications that lead to the growth of the urban area when compared to those granted applications permitting other forms of development, such as that linked to minor modifications to existing buildings and restoration works amongst others. Nonetheless, the absolute number of granted development-planning applications resulting in growth has increased, particularly in the last construction boom (post 2013). The share of applications denoting growth granted within the development zone has remained stable throughout the years. The years with the highest numbers of permits granted outside the development zone, where there was a disposition against development, were 2017 and 2018. In conclusion, the trends and patterns resulting from development cycles were analysed and discussed. The outcomes of this work will lead to better measurement of urban growth in Malta and assess the efficacy of current national development-planning policies. This is in line with the UN’s Sustainable Development Goal 11, which aims at making “cities and human settlements inclusive, safe, resilient, and sustainable”. The research specifically addresses Target 11a, which is focused on supporting “positive economic, social, and environmental links between urban, peri-urban, and rural areas by strengthening national and regional development planning”.