Industrially generated trans-fats have been linked with cardiovascular disease (CVD) and have thus been replaced by interesterified (IE) fats, in foods. Interesterification rearranges fatty acids on the glycerol backbone of a triacylglycerol molecule. However, the impact of IE fat on health is unknown. We recently reported differences in lipid absorption kinetics between IE and rapeseed oil (RO). Here, we investigated the mechanisms underpinning IE fat digestion kinetics in the same muffins baked using an IE fat, non-IE fat [with the same fatty acid composition] and rapeseed oil (RO) under simulated conditions. IE and non-IE fats were largely solid in the gastric phase and strongly associated within the muffin matrix, whereas RO formed liquid droplets which separated from the matrix. No significant difference in lipolysis rates was detected between IE and non-IE fats. The lipolysis of the RO fat was slower, due to long-chain PUFAs. Interesterification itself did not affect digestibility, but the strong interaction between the hard fats and the muffin matrix resulted in extensive creaming of the matrix in the stomach, leading to delayed gastric emptying compared to the RO sample. The rate and extent of lipolysis were determined by the amount of fat available and the structure of the fat. This demonstrates the importance of the physical behaviour of the fats during digestion and provides a mechanistic understanding of the overall lipid digestion of IE fats, which relates to their physiological response.