We propose a novel process for the production of a DAG-rich acylglycerol mixture derived from milk fat. This product has potentially interesting nutritional properties, derived from both its high content of DAG and of short-chain fatty acids (FAs). The proposed process consists of three steps: lipase-catalysed partial ethanolysis of milk fat, extraction of the by-product fatty acid ethyl esters (FAEEs) using supercritical carbon dioxide (SC-CO2) and isomerization of DAG to increase the proportion of 1,3-DAG. The experimental investigation of the process steps was done using milk fat and trilaurin. Several lipases were tested for maximizing the percentage of DAG in the acylglycerol mixture produced by ethanolysis. The selectivity of the chosen lipase was such that the produced AG mixture was enriched in short-chain FAs in relation to the original milk fat. FAEEs were completely extracted from the ethanolysis mixture by SC-CO2. In the final process step, we explored the reaction conditions for facilitating acyl migration in the DAG mixture, so that the equilibrium proportion of 1,3-DAG (∼64%) was attained. Our results set the basis for the development of a simple process for the production of a DAG-rich milk fat analogue.