Oils often have similar properties and can be difficult to identify based on color, smell or taste alone. The present paper suggests the use of Fourier-transform infrared spectroscopy (FTIR) in combination with chemometric methods to explore similarities and differentiate between samples of Moldavian dragonhead oil subjected to different storage conditions. Dragonhead is a plant characterized by very good honey output and ease of cultivation. Principal component analysis (PCA) was applied to a standard, full range of FTIR spectra. Additionally, hierarchical cluster analysis (HCA) was employed to explore the organization of the samples in groups relative to their “proximity” (similarity), by way of Euclidean distance measurement. PC1 and PC2 accounted respectively for 85.4% and 10.1% of the total data variance. PC1 and PC2 were strongly, negatively correlated within the entire spectral range; the only exception was the region corresponding to νs(-C-Hvst, -CH2) vibrations (aliphatic groups in triglycerides), where PC2 was positively correlated. The use of FTIR spectral analysis revealed noticeable differences in the intensity of bands characteristic of the ageing processes (markers of oxidative processes, etc.) taking place in oleaginous samples and related to the processes of fatty acids oxidation.