The present study aims to investigate the in vitro intestinal digestion fate of Pickering emulsions with complex dual particle interfaces. Pickering oil-in-water emulsions (PPM-E) stabilized by plant (pea) protein-based microgels (PPM), as well as PPM-E where the interface was additionally covered by cellulose nanocrystals (CNC), were designed at acidic pH (pH 3.0). The gastrointestinal fate of the PPM-E and free fatty acid (FFA) release, was tested via the INFOGEST static in vitro digestion model and data was fitted using theoretical models. Lipid digestion was also monitored using lipase alone bypassing the gastric phase to understand the impact of proteolysis on FFA release. Coalescence was observed in the PPM-stabilized emulsions in the gastric phase, but not in those co-stabilized by CNC. However, coalescence occurred during the intestinal digestion stage, irrespective of the CNC concentration added (1–3 wt % CNC). The presence of CNC lowered the lipolysis kinetics but raised the extent of FFA release as compared to in its absence (p < 0.05), due to lower levels of gastric coalescence, i.e., a higher interfacial area. The trends were similar when just lipase was added with no prior gastric phase, although the extent and rate of FFA release was reduced in all emulsions, highlighting the importance of prior proteolysis in lipolysis of such systems. In summary, an electrostatically self-assembled interfacial structure of two types of oppositely-charged particles (at gastric pH) might be a useful strategy to enable enhanced delivery of lipophilic compounds that require protection in the stomach but release in the intestines.