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Throughout history there have been numerous examples of military underdogs beating the odds, despite what conventional warfare theory says. Studies about this phenomenon are categorized asasymmetric warfare theories. But, upon examination of previous research, the studies seemprimarily centered on the strategic level rather than the tactical. The research problem, therefore, is the lack of asymmetric warfare theories on the lower levels of war, and more specifically thelack of such theories in intergovernmental land conflicts. The purpose of this study is to contribute to this research by testing an existing asymmetric airpower theory, The Underdog’s Model by Arash Heydarian Pashakhanlou, in a land warfare-context. Through an operationalization based on the core concepts of both airpower and land warfare, the study offers a translated model (U_m) which can inform weaker nations on how to act. Using a qualitative theory-testing design and qualitative text analysis, the model is applied to two battles from the Finnish Winter War, the second battle of Summa and the battle of Tolvajärvi. The results show that the model possesses high explanatory power in both cases: the defeat at Summa is explained by underperformance by Finland in the theory's six factors, while the success at Tolvajärvi is explained by high performance in the same factors. Future research is encouraged to apply this theory in studies with other research designs for further generalizability.