Exploring post-conflict landscapes is both complex and controversial in heritage studies. Where the past is still a part of living memory, the act of remembering and forgetting means that even amongst those that largely agree on what occurred, there will still be discrepancies and disagreements. This poses challenges for those studying legacies of past conflict. Rather than promote an 'authorised' account of the past however, there is scope to adopt more inclusive approaches to address risky and contested heritage. This thesis does this by using Deep Mapping as a holistic approach to explore and understand complex and contested pasts in the field of (post-)conflict archaeology. Deep Mapping is gaining wider currency in the humanities, and especially digital humanities, as scholars struggle to view and analyse the 'digital deluge' of data increasingly available to them. However, Deep Maps and Deep Mapping has been largely ignored by archaeologists despite its potential to handle complex, multi-vocal history. This may in part be due to the fact Deep Maps remain under theorised and methodologically diffuse. To this end, this thesis provides the first detailed exploration of what renders a map 'deep', by tracing the concept of Deep Mapping and defining and developing a transferable methodology to assist in the research of post-conflict landscapes. The methodology is formed through combining landscape archaeology, oral histories, and Geographic Information Systems (GIS). With an empirical focus on the archaeologies of former World War II military airfields in Northern Ireland as well-founded exemplars, key findings of the research include Deep Mapping's potential for aiding academic enquiry into complex and controversial landscapes by enabling a framework which incorporates past, present and future knowledge and understandings. The thesis explores Deep Mapping methodologies through three steps, starting first with creating a GIS-based series of landscape layers from historic and modern maps, aerial imagery, and archaeological evidence, then secondly drawing on local oral histories, and thirdly, integrating these to create an interactive, deeper mapping experience. The thesis contributes more widely to questions in conflict archaeology, historical and cultural geography, critical cartography, and landscape studies. The result of this thesis is a fully documented, multi-faceted, series of exemplar Deep Maps based on the unique and important history of Northern Ireland military airfields over time, a literature review reflecting the current state-of-the-art in the application of Deep Maps, and a nuanced and further developed methodology which presents the opportunities and challenges of using Deep Maps in scholarship and as way of sharing complex material holistically.