The potential gastrointestinal fate of oil-in-water emulsions containing lipid phases from different sources was examined: vegetable oils (corn, olive, sunflower, and canola oil); marine oils (fish and krill oil); flavor oils (orange and lemon oil); and, medium chain triglycerides (MCT). The lowest rates and extents of lipid digestion were observed for emulsified flavor oil, followed by emulsified krill oil. There was no appreciable difference between the final amounts of free fatty acids released for emulsified digestible oils. Differences in the digestibility of emulsions prepared using different oils were attributed to differences in their compositions, e.g., fatty acid chain length and unsaturation. The particle size distribution, particle charge, microstructure, and macroscopic appearance of the emulsions during passage through the simulated GIT depended on oil type. The results of this study may facilitate the design of functional foods that control the digestion and absorption of triglycerides, as well as the bioaccessibility of hydrophobic bioactives.