Amphiphilic esterified maltodextrin palmitate (DE9_P) is synthesized using an enzyme-catalyzed reaction and exhibits both emulsifying and stabilizing activity. Native maltodextrin with a dextrose equivalent of nine (DE9) and DE9_P are applied in Tween 80-stabilized oil-in-water emulsions. The effects of different DE9/DE9_P concentrations (10-50% w/w) on in vitro gastrointestinal digestibility of the Tween 80-stabilized emulsions are investigated. After complete digestion, at a low DE9/DE9_P concentration (10% w/w), the released free fatty acid (FFA) content of the Tween 80-stabilized emulsion containing DE9_P (13%) is much lower than that of the emulsion containing DE9 (33%) because of the synergistic Tween 80 and DE9_P stabilization layer. As the concentration increases to 30% w/w, the released FFA content increases for both systems containing DE9 and DE9_P. However, the emulsion system with DE9_P still has a lower content of released FFA than for DE9. Further increasing the concentration to 50% w/w results in a clear decrease in the released FFA content for both emulsions because the highly viscous continuous phase may cause less digestive reaction. The oil-water interfacial stabilization layer and the viscosity of the intestinal digested system may be important factors in the enhancement or inhibition of lipid digestion. Practical Applications: The application of the potential ingredients at suitable concentrations enables the design and control of lipid digestibility and the texture of products to satisfy consumers' needs. DE9_P may be an attractive alternative ingredient for emulsified foods because it can function both via synergistic emulsion stabilization with Tween 80 and via modification of textural characteristics as a stabilizer. Moreover, DE9_P has greater efficacy than DE9 in the inhibition of lipid digestibility of Tween 80-stabilized oil-in-water emulsions.