A commercial preparation of medium-chain TAG (MCT) was enzymatically transesterified with a fully hydrogenated soybean oil (FHSBO) at different weight ratios (40:60, 50:50, 60:40, and 70:30). All reactions were carried out at 70 °C in flasks placed in an orbital shaker (300 rpm). Three different lipase preparations were tested: TLIM (Thermomyces lanuginosus), lipase PS (Burkholderia cepacia), and Chirazyme L2 (Candida antarctica). The progress of the reaction was monitored by following the changes in the triacylglycerol (TAG) profile of the reaction mixture with reversed-phase high-performance liquid chromatography (HPLC). The rates of disappearance of the TAG originally present in both the MCT and the FHSBO were fastest when lipase TL IM was used; the slowest rates were observed for lipase PS. Although the relative compositions of the newly formed TAG at equilibrium depended on the particular lipase used and the initial weight ratio of the substrates, the TAG families containing 2 stearic residues and a residue of either capric acid or caprylic acid were the most abundant product species. All samples were analyzed by differential scanning calorimetry (DSC) to determine the effect of this reaction on the melting profile of the resulting products.