One of the commonly used food preparation methods is frying. Fried food is admired by consumers due to its unique taste and texture. Deep frying is a process of dipping food in oil at high temperature, usually 170–190 °C, and it requires a relatively short time. The aim of this study was to analyze the thermo-oxidative changes occurring during the deep frying of products such as potatoes and tofu in cold pressed rapeseed oils and palm olein. Cold pressed rapeseed oil from hulled seeds (RO), cold pressed high oleic rapeseed oil from hulled seeds (HORO), and palm olein (PO) (for purposes of comparison) were used. Characterization of fresh oils (after purchase) and oils after 6, 12, and 18 h of deep frying process of a starch product (potatoes) and a protein product (tofu) was performed. The quality of oils was analyzed by determining peroxide value, acid value, p-anisidine value, content of carotenoid and chlorophyll pigments, polar compounds, smoke point, color (CIE L*a*b*), fatty acids content and profile, calculation of lipid nutritional quality indicators, and oxidative stability index (Rancimat). Cold pressed high oleic rapeseed oil was more stable during deep frying compared to cold pressed rapeseed oil, but much less stable than palm olein. In addition, more thermo-oxidative changes occurred in the tested oils when deep frying the starch product (potatoes) compared to the deep frying of the protein product (tofu).