In Slovenia two superb vegetable oils with high added nutritional value are produced: "Ekstra devisko oljcno olje Slovenske Istre (extra virgin olive oil from Slovene Istra)" and "Stajersko prekmursko bucno olje (pumpkin seed oil from Slovenia)". Their quality and genuineness must be monitored as adulteration can easily be undertaken. Olive oil genuineness determination experiences can show how analyses following an experience data-driven decision tree gathering several chemical determinations (fatty acids, (E)-isomers of fatty acids, sterol and tocopherol determinations) may be helpful in assessing the pumpkin seed oil from Slovenia genuineness. In the present work a set of HPLC triacylglycerol determinations was performed, based on the nine main triacylglycerols (LLLn, LLL, PLL, LOO, PLO, OOO, POO, SPL, and SLS) on a limited number of different pumpkin seed oils from northeastern Slovenia. The performed determinations showed that stereospecific analyses of triacylglycerols together with other chemical determinations can be useful in building a protocol for the evaluation of the genuineness of pumpkin seed oil from Slovenia.