Health benefits are associated with polyunsaturated fatty acids, but their sensitivity to oxidation may generate toxic oxidation species. The objective of this study was to compare the effect of milk proteins (casein, whey protein) and surfactants (Citrem, Tween 20) on the in vitro digestion and oxidation of linseed oil emulsions. The emulsion produced with Tween 20 resisted coalescence in the gastric phase and showed the highest concentrations of free fatty acids and reactive carbonyl compounds in the intestinal digestion phase. The Citrem-stabilized emulsion showed extensive coalescence in the gastric environment, which reduced lipolysis and the formation of advanced oxidation species. The protein-stabilized emulsions showed aggregation with some coalescence in the gastric phase, and casein provided better protection than whey protein against oxidation. This study suggests that the mechanism of emulsion destabilization in the gastric environment and the type of protein can modulate lipolysis and oxidation during in vitro digestion.