Most current research on food-relevant Pickering emulsions has been conducted using inorganic or food-compatible organic particles as emulsifiers. A key challenge is maintaining a favourable structure while being able to resist displacement or destabilisation by surfactants and controlling transport of substrates during digestion. Liposome stabilised emulsions have demonstrated some potential for being smart, responsive delivery systems for poorly available bioactives and drugs. We developed a liposome-stabilized oil-in-water Pickering emulsion utilising macromolecular crowding- with polyethylene glycol (PEG). They were pH-controllable and had surfactant-dependent deformability whilst displaying dual delivery routes from both the liposome and oil phases. Dynamic light scattering, confocal microscopy and emulsion stability measurements indicated the liposomes containing 10% PEG at neutral pH remained intact at the interface for extended time. Various degrees of interfacial coverage still existed in the presence of PEG, under acidic environment and with added bile salts. Emulsions with added PEG maintained a more integrated structure after in vitro oral-gastric digestion, and showed greater lipolysis with more free fatty acids (14.7 ± 0.5% for with PEG vs. 12.7 ± 0.1% for without PEG) released during in vitro intestinal digestion. These Pickering emulsions could provide a flexible approach to controlled release under a broad range of conditions.