Albanian olive genetic resources remain under-characterised despite their potential for differentiated oil production. We evaluated 11 authenticated cultivars conserved in the Vlorë germplasm collection under common field, maturity and standardised industrial three-phase extraction conditions. Phenolics profile of those cultivars was quantified by liquid chromatography–tandem mass spectrometry (LC-MS/MS), and fatty-acid composition was determined by gas chromatography with flame-ionisation detection (GC-FID). Also, fruit moisture and oil content were analysed in maturity index 3. All these analytical parameters were integrated through univariate and multivariate statistical analyses. Cultivar factor significantly affected every trait. Total quantified phenolics ranged from 296.5 mg kg⁻¹ in ‘U.K. Berat’ to 791.0 mg kg⁻¹ in ‘Managjel FV’; the latter was oleocanthal-rich, whereas ‘U.H. Himare’, ‘Pulazeqin’, ‘Ulliri i Kuq’ and ‘Kotruvsi’ showed distinctive oleacein-, oleuropein-aglycone/oleomissional-, ligstroside-aglycone/tyrosol-, and luteolin/hydroxytyrosol-rich profiles, respectively. Oleic acid ranged from 65.36% in ‘Kotruvsi’ to 79.92% in ‘Unafka’, which also showed the highest oleic/linoleic ratio. All cultivar means in this study exceeded the 250 mg kg⁻¹ screening reference for the European Food Safety Authority (EFSA)-related phenolic content, thereby showcasing the potential of Albanian monovarietal oils with respect to their health properties. Multivariate analyses provided complementary chemical and technological classification rather than a single quality ranking. These cultivar fingerprints provide a basis for conservation, breeding, authenticity assessment and future Protected Designation of Origin (PDO)/Protected Geographical Indication (PGI) valorisation.